Heterocyclic compound and harmful arthropod-controlling composition containing same

Abstract

A compound of formula (I) or its N-oxide,where Z represents an oxygen atom or the like; G1 represents CR3a or the like; G2 represents CR3b or the like; G3 represents CR3c or the like; G4 represents CR3d or the like; A1 represents CR4a or the like; A2 represents CR4b or the like; A3 represents CR4c or the like; A4 represents CR4d or the like; A5 represents CR4c or the like; R1 represents a C1-C6 chain hydrocarbon group or the like; R2 represents a C1-C6 alkyl group or the like; R3a, R3b, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group or the like; R4a, R4b, R4c, R4d, and R4e are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group or the like; and n represents 0, 1, or 2.

Description

US_SUMMARY_OF_INVENTIONCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] The present application is a 35 U.S.C. § 371 national stage patent application of International patent application PCT / JP2021 / 035965, filed on Sep. 29, 2021, which is based on and claims the benefits of priority to Japanese Application No. 2020-165684, filed on Sep. 30, 2020 and Japanese Application No. 2021-102389, filed on Jun. 21, 2021. The entire contents of all of the above applications are incorporated herein by reference.TECHNICAL FIELD

[0002] This patent application claims the priorities to and the benefits under the Paris convention of Japanese Patent Application No. 2020-165684 filed on Sep. 30, 2020 and Japanese Patent Application No. 2021-102389 filed on Jun. 21, 2021, the entire contents of which are incorporated herein by reference.

[0003] The present invention relates to heterocyclic compounds and compositions for controlling harmful arthropods comprising the same.BACKGROUND ART

[0004] To date, various compounds have been studied in order to control harmful arthropods. For example, Patent Document 1 discloses that certain kinds of compounds have control effects on pests.CITATION LISTPatent Document

[0005] Patent Document 1: WO 2016 / 129684 pamphletSUMMARY OF THE INVENTIONProblems to be Solved by Invention

[0006] An object of the present invention is to provide compounds having excellent control efficacy against harmful arthropods.Means to Solve Problems

[0007] The present invention provides the followings.[1] A compound represented by formula (I)

[0008] [wherein:

[0009] Z represents an oxygen atom or a sulfur atom;

[0010] R1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent (s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group U, a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, C(O)R51, C(O)OR51, or C(O)NR51R52;

[0011] R51 and R52 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, or a hydrogen atom;

[0012] R2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;

[0013] n represents 0, 1, or 2;

[0014] G1 represents a nitrogen atom or CR3a;

[0015] G2 represents a nitrogen atom or CR3b;

[0016] G3 represents a nitrogen atom or CR3c;

[0017] G4 represents a nitrogen atom or CR3d;

[0018] R3a, R3b, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group E, a phenyl group optionally substituted with one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group H, OR12, NR11R12, NR11aR12a, NR24NR11R12, NR24OR11, NR11C(O)R13, NR24NR11C(O)R13, NR11C(O)OR14, NR24NR11C(O)OR14, NR11C(O)NR31R32, NR24NR11C(O)NR31R32, N═CHNR31R32, N═S(O)pR15R16, C(O)R13, C(O)OR17, C(O)NR31R32, C(O)NR11S(O)2R23, CR30═NOR17, NR11CR24═NOR17, S(O)mR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom;

[0019] p represents 0 or 1;

[0020] m represents 0, 1, or 2;

[0021] R30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a halogen atom, OR35, NR36R37, or a hydrogen atom;

[0022] R35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);

[0023] R17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;

[0024] R11, R24, R36, and R37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom;

[0025] R12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group J, a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a hydrogen atom, or S(O)2R23;

[0026] R23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s) or a phenyl group optionally substituted with one or more substituent(s) selected from Group D;

[0027] R11a and R12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E;

[0028] R13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;

[0029] R14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), or a phenyl C1-C3 alkyl group {wherein the phenyl moiety in said phenyl C1-C3 alkyl group is optionally substituted with one or more substituent(s) selected from Group D};

[0030] R15 and R16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);

[0031] R31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;

[0032] R32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, S(O)2R23, or a hydrogen atom;

[0033] A1 represents a nitrogen atom or CR4a;

[0034] A2 represents a nitrogen atom or CR4b;

[0035] A3 represents a nitrogen atom or CR4c;

[0036] A4 represents a nitrogen atom or CR4d;

[0037] A5 represents a nitrogen atom or CR4e;

[0038] provided that not all of A2, A3, and A4 represent nitrogen atoms;

[0039] R4a and R4e are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O)kR41, S(O)2NR41R42, NR41R43, NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

[0040] when A5 represents CR4e, R4e and R1 are optionally combined with each other to form —NR45—CR41R42-#{wherein # represents the binding position to the nitrogen atom to which R1 is bound};

[0041] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O)qR41, S(O)2NR41R42, NR41R42, NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

[0042] provided that not all of present R4a, R4b, R4c, R4d, and R4e represent hydrogen atoms;

[0043] k represents 0, 1, or 2;

[0044] q represents 0, 1, or 2;

[0045] R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;

[0046] R43 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, or a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z;

[0047] R44 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);

[0048] R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W2, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, C(O)R46, C(O)OR46, C(O)NR46R47, or a hydrogen atom; and

[0049] R46 and R47 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;

[0050] Group B: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a cyano group, a hydroxy group, and a halogen atom;

[0051] Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), and a halogen atom;

[0052] Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom;

[0053] R21 and R22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);

[0054] Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;

[0055] Group F: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group C, an amino group, NHR21, NR21R22, a halogen atom, and a cyano group;

[0056] Group H: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, OR10, NR9R10, C(O)R10, C(O)NR9R10, OC(O)R9, OC(O)OR9, NR10C(O)R9, NR10C(O)OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, and an amino group;

[0057] R9 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s) or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s);

[0058] R10 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;

[0059] Group J: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, and a cyano group;

[0060] Group U: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;

[0061] Group V: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;

[0062] Group W: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a cyano group, and a halogen atom;

[0063] Group X: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom;

[0064] Group Y: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;

[0065] Group Z: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;

[0066] Group W2: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom]

[0067] (hereinafter referred to as “Present compound P” or “Compound P of the present invention”) or an N-oxide thereof (hereinafter the compound represented by formula (I) or an N-oxide thereof is referred to as “Present compound X” or “Compound X of the resent invention”).[2] The compound according to [1], wherein

[0068] R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, C(O)R46, C(O)OR46, C(O)NR46R47, or a hydrogen atom (hereinafter referred to as “Present compound N” or “Compound N of the present invention”) or an N-oxide thereof (hereinafter the Present compound N or an N-oxide thereof is referred to as “Present compound” or “Compound of the present invention”).[3] The compound or an N-oxide thereof according to [1] or [2], wherein

[0069] G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3d.[4] The compound or an N-oxide thereof according to any one of [1] to [3], wherein

[0070] A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom or CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents a nitrogen atom or CR4e.[5] The compound or an N-oxide thereof according to any one of [1] to [3], whereinthe combination of A1, A2, A3, A4, and A5 represents:

[0072] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents CR4e;

[0073] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e;

[0074] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom, and A5 represents CR4e; or

[0075] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom.[6] The compound or an N-oxide thereof according to any one of [1] to [3], wherein

[0076] A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents CR4e.[7] The compound or an N-oxide thereof according to [1] or [2], wherein

[0077] G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d; and

[0078] A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents CR4e.[8] The compound or an N-oxide thereof according to any one of [1] to [7], wherein R2 represents an ethyl group.[9] The compound or an N-oxide thereof according to any one of [1] to [8], wherein Z represents an oxygen atom.

[10] A composition for controlling a harmful arthropod comprising the compound or an N-oxide thereof according to any one of [1] to [9].

[11] A composition comprising one or more ingredient(s) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the compound or an N-oxide thereof according to any one of [1] to [9]:

[0079] Group (a): a group consisting of insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients;

[0080] Group (b): fungicidal active ingredients;

[0081] Group (c): plant growth regulatory ingredients;

[0082] Group (d): repellent ingredients.

[12] A method for controlling a harmful arthropod which comprises applying an effective amount of the compound or an N-oxide thereof according to any one of [1] to [9] or an effective amount of the composition according to

[11] to a harmful arthropod or a habitat where a harmful arthropod lives.

[13] A seed or a vegetative reproductive organ holding an effective amount of the compound or an N-oxide thereof according to any one of [1] to [9] or an effective amount of the composition according to

[11] .

[14] A compound represented by formula (II)

[0083] [wherein the symbols are the same as defined above,]or a salt thereof (hereinafter the compound represented by formula (II) or a salt thereof is referred to as “Intermediate compound A”).Effect of Invention

[0084] According to the present invention, harmful arthropods can be controlled.MODE FOR CARRYING OUT THE INVENTION

[0085] The substituents in the present invention are explained as follows.

[0086] The term of “halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0087] When a substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be identical to or different from each other.

[0088] The expression of “CX-CY” as described herein means that the number of carbon atom is X to Y. For example, the expression of “C1-C6” means that the number of carbon atom is 1 to 6.

[0089] The term of “chain hydrocarbon group” represents an alkyl group, an alkenyl group, or an alkynyl group.

[0090] Examples of the term of “alkyl group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0091] Examples of the term of “alkenyl group” include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 1-ethyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group, and a 5-hexenyl group.

[0092] Examples of the term of “alkynyl group” include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-ethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, and a 5-hexynyl group.

[0093] Examples of the term of “alkoxy group” include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.

[0094] Examples of the term of “alkenyloxy group” include a 2-propenyloxy group, a 2-butenyloxy group, and a 5-hexenyloxy group.

[0095] Examples of the term of “alkynyloxy group” include a 2-propynyloxy group, a 2-butynyloxy group, and a 5-hexynyloxy group.

[0096] Examples of the term of “cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0097] Examples of the term of “cycloalkenyl group” include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0098] The term of “3-7 membered nonaromatic heterocyclic group” represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring.

[0099] Examples of the term of “3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E” include the following groups,

[0100]

[0101] The term of “5 or 6 membered aromatic heterocyclic group” represents a 5 membered aromatic heterocyclic group or a 6 membered aromatic heterocyclic group. The term of “5 membered aromatic heterocyclic group” represents a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. The term of “6 membered aromatic heterocyclic group” represents a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group.

[0102] The term of “5 or 6 membered heterocyclic group” represents a 5 or 6 membered aromatic heterocyclic group or a 5 or 6 membered nonaromatic heterocyclic group, and examples thereof include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a pyrrolidinyl group, an imidazolinyl group, an imidazolidinyl group, a piperidinyl group, a tetrahydropyrimidinyl group, a hexahydropyrimidinyl group, a piperazinyl group, an oxazolidinyl group, an isoxazolidinyl group, a 1,3-oxazinanyl group, a morpholinyl group, a thiazolidinyl group, an isothiazolidinyl group, a 1,3-thiazinanyl group, and a thiomorpholinyl group.

[0103] Examples of the term of “(C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s)” include a cyclopropylmethyl group, a (2-fluorocyclopropyl)methyl group, a cyclopropyl(fluoro)methyl group, and a (2-fluorocyclopropyl) (fluoro)methyl group.

[0104] Examples of the term of “phenyl C1-C3 alkyl group {wherein the phenyl moiety in said phenyl C1-C3 alkyl group is optionally substituted with one or more substituent(s) selected from Group D}” include a benzyl group, a 2-fluorobenzyl group, a 4-chlorobenzyl group, a 4-(trifluoromethyl)benzyl group, and a 2-[4-(trifluoromethyl)phenyl]ethyl group.

[0105] Examples of the term of “alkylsulfanyl group” include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.

[0106] Examples of the term of “alkylsulfinyl group” include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group.

[0107] Examples of the term of “alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

[0108] Examples of the term of “alkylamino group” include a methylamino group, an ethylamino group, an isopropylamino group, and a hexylamino group.

[0109] Examples of the term of “dialkylamino group” include a dimethylamino group, an ethylmethylamino group, an isopropylmethylamino group, and a dihexylamino group.

[0110] Examples of the term of “alkylcarbonyl group” include an acetyl group, a propanoyl group, a 2-methylpropanoyl group, and a hexanoyl group.

[0111] Examples of the term of “alkoxycarbonyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, and a pentyloxycarbonyl group.

[0112] In R4a, R4b, R4c, R4d, and R4e, the expression of “provided that not all of present R4a, R4b, R4c, R4d, and R4e represent hydrogen atoms” means that the 6 membered ring containing A1, A2, A3, A4, and A5 (namely, a phenyl group or a 6 membered aromatic heterocyclic group) has one or more substituent (s), and that at least one of present R4a, R4b, R4c, R4d, and R4e is not a hydrogen atom. For example, in the compounds wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4a, and A5 represents CR4a, the compounds wherein all of R4a, R4b, R4c, R4d, and R4a are hydrogen atoms are excluded, and in the compounds wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom, and A5 represents CR4b, the compounds wherein all of R4a, R4b, R4c, and R4e are hydrogen atoms are excluded.

[0113] In other words, in formula (I) or formula (II), a phenyl group or a 6 membered aromatic heterocyclic group represented by formula (I-P)

[0114] [wherein the wavy line represents the binding position to C(Z); and the other symbols are the same as defined above.] is not unsubstituted.

[0115] Examples of the N-oxide of the compound represented by formula (I) include a compound represented by the following formula.

[0116] [wherein the symbols are the same as defined above.]

[0117] The Present compound X and the Intermediate compound A may optionally have one or more stereoisomer (s). Examples of the stereoisomer(s) include enantiomers, diastereomers, and geometric isomers. The Present compound X and the Intermediate compound A encompass each stereoisomer and mixtures of stereoisomers at any ratio.

[0118] The Present compound X and the compound represented by formula (II) may optionally form an acid addition salt. Examples of the acid to form the acid addition salt include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid; and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. Such acid addition salt may be prepared by mixing the Present compound X or the compound represented by formula (II) with an acid.

[0119] Aspects of the Present compound N include the following compounds.[Aspect 1] The Present compound N, whereinR1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W;

[0121] when A5 represents CR4e, R4e and R1 are optionally combined with each other to form —NR45—CR41R42-#;

[0122] R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0123] R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, or a hydrogen atom.[Aspect 2] The Present compound N, wherein

[0124] R1 represents a C1-C6 alkyl group;

[0125] when A5 represents CR4e, R4e and R1 are optionally combined with each other to form —NR45—CR41R42-#; and

[0126] R41, R42, and R45 are identical to or different from each other, and each represent a C1-C6 alkyl group or a hydrogen atom.[Aspect 3] The Present compound N, wherein

[0127] the combination of G1, G2, G3, and G4 represents:

[0128] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3d;

[0129] a combination wherein G1 represents a nitrogen atom, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0130] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0131] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3a;

[0132] R3a, R3c, and R3d each represent a hydrogen atom; and

[0133] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 4] The Present compound N, wherein

[0134] G1 represents CR3a;

[0135] G2 represents CR3b;

[0136] G3 represents CR3c;

[0137] G4 represents a nitrogen atom or CR3d;

[0138] R3a, R3c, and R3d each represent a hydrogen atom; and

[0139] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 5] The Present compound N, wherein

[0140] G1 represents CR3a;

[0141] G2 represents CR3b;

[0142] G3 represents CR3c;

[0143] G4 represents a nitrogen atom or CR3d;

[0144] R3a, R3c, and R3d each represent a hydrogen atom; and

[0145] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 6] The Present compound N, wherein

[0146] G1 represents CR3a;

[0147] G2 represents CR3b;

[0148] G3 represents CR3c;

[0149] G4 represents CR3d;

[0150] R3a, R3c, and R3d each represent a hydrogen atom; and

[0151] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 7] The Present compound N, wherein

[0152] G1 represents CR3a;

[0153] G2 represents CR3b;

[0154] G3 represents CR3c;

[0155] G4 represents CR3a;

[0156] R3a, R3c, and R3d each represent a hydrogen atom; and

[0157] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 8] The compound according to the Aspect 1, wherein

[0158] the combination of G1, G2, G3, and G4 represents:

[0159] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3d;

[0160] a combination wherein G1 represents a nitrogen atom, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0161] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0162] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3d;

[0163] R3a, R3c, and R3d each represent a hydrogen atom; and

[0164] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 9] The compound according to the Aspect 2, wherein

[0165] the combination of G1, G2, G3, and G4 represents:

[0166] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3a;

[0167] a combination wherein G1 represents a nitrogen atom, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0168] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0169] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3a;

[0170] R3a, R3c, and R3d each represent a hydrogen atom; and

[0171] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 10] The compound according to the Aspect 1, wherein

[0172] G1 represents CR3a;

[0173] G2 represents CR3b;

[0174] G3 represents CR3c;

[0175] G4 represents a nitrogen atom or CR3d;

[0176] R3a, R3c, and R3d each represent a hydrogen atom; and

[0177] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 11] The compound according to the Aspect 2, wherein

[0178] G1 represents CR3a;

[0179] G2 represents CR3b;

[0180] G3 represents CR3c;

[0181] G4 represents a nitrogen atom or CR3d;

[0182] R3a, R3c, and R3d each represent a hydrogen atom; and

[0183] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 12] The compound according to the Aspect 1, wherein

[0184] G1 represents CR3a;

[0185] G2 represents CR3b;

[0186] G3 represents CR3c;

[0187] G4 represents a nitrogen atom or CR3d;

[0188] R3a, R3c, and R3d each represent a hydrogen atom; and

[0189] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 13] The compound according to the Aspect 2, wherein

[0190] G1 represents CR3a;

[0191] G2 represents CR3b;

[0192] G3 represents CR3c;

[0193] G4 represents a nitrogen atom or CR3d;

[0194] R3a, R3c, and R3d each represent a hydrogen atom; and

[0195] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 14] The compound according to the Aspect 1, wherein

[0196] G1 represents CR3a;

[0197] G2 represents CR3b;

[0198] G3 represents CR3c;

[0199] G4 represents CR3d;

[0200] R3a, R3c, and R3d each represent a hydrogen atom; and

[0201] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 15] The compound according to the Aspect 2, wherein

[0202] G1 represents CR3a;

[0203] G2 represents CR3b;

[0204] G3 represents CR3c;

[0205] G4 represents CR3d;

[0206] R3a, R3c, and R3d each represent a hydrogen atom; and

[0207] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect 16] The compound according to the Aspect 1, wherein

[0208] G1 represents CR3a;

[0209] G2 represents CR3b;

[0210] G3 represents CR3c;

[0211] G4 represents CR3d;

[0212] R3a, R3c, and R3d each represent a hydrogen atom; and

[0213] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 17] The compound according to the Aspect 2, wherein

[0214] G1 represents CR3a;

[0215] G2 represents CR3b;

[0216] G3 represents CR3c;

[0217] G4 represents CR3d;

[0218] R3a, R3c, and R3d each represent a hydrogen atom; and

[0219] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect 18] The Present compound N, wherein

[0220] Z represents an oxygen atom; and

[0221] R2 represents a C1-C6 alkyl group.[Aspect 19] The Present compound N, wherein

[0222] Z represents an oxygen atom; and

[0223] R2 represents an ethyl group.[Aspect 20] The compound according to the Aspect 1, wherein

[0224] Z represents an oxygen atom; and

[0225] R2 represents a C1-C6 alkyl group.[Aspect 21] The compound according to the Aspect 2, wherein

[0226] Z represents an oxygen atom; and

[0227] R2 represents a C1-C6 alkyl group.[Aspect 22] The compound according to the Aspect 3, wherein

[0228] Z represents an oxygen atom; and

[0229] R2 represents a C1-C6 alkyl group.[Aspect 23] The compound according to the Aspect 4, wherein

[0230] Z represents an oxygen atom; and

[0231] R2 represents a C1-C6 alkyl group.[Aspect 24] The compound according to the Aspect 5, wherein

[0232] Z represents an oxygen atom; and

[0233] R2 represents a C1-C6 alkyl group.[Aspect 25] The compound according to the Aspect 6, wherein

[0234] Z represents an oxygen atom; and

[0235] R2 represents a C1-C6 alkyl group.[Aspect 26] The compound according to the Aspect 7, wherein

[0236] Z represents an oxygen atom; and

[0237] R2 represents a C1-C6 alkyl group.[Aspect 27] The compound according to the Aspect 8, wherein

[0238] Z represents an oxygen atom; and

[0239] R2 represents a C1-C6 alkyl group.[Aspect 28] The compound according to the Aspect 9, wherein

[0240] Z represents an oxygen atom; and

[0241] R2 represents a C1-C6 alkyl group.[Aspect 29] The compound according to the Aspect 10, wherein

[0242] Z represents an oxygen atom; and

[0243] R2 represents a C1-C6 alkyl group.[Aspect 30] The compound according to the Aspect 11, wherein

[0244] Z represents an oxygen atom; and

[0245] R2 represents a C1-C6 alkyl group.[Aspect 31] The compound according to the Aspect 12, wherein

[0246] Z represents an oxygen atom; and

[0247] R2 represents a C1-C6 alkyl group.[Aspect 32] The compound according to the Aspect 13, wherein

[0248] Z represents an oxygen atom; and

[0249] R2 represents a C1-C6 alkyl group.[Aspect 33] The compound according to the Aspect 14, wherein

[0250] Z represents an oxygen atom; and

[0251] R2 represents a C1-C6 alkyl group.[Aspect 34] The compound according to the Aspect 15, wherein

[0252] Z represents an oxygen atom; and

[0253] R2 represents a C1-C6 alkyl group.[Aspect 35] The compound according to the Aspect 16, wherein

[0254] Z represents an oxygen atom; and

[0255] R2 represents a C1-C6 alkyl group.[Aspect 36] The compound according to the Aspect 17, wherein

[0256] Z represents an oxygen atom; and

[0257] R2 represents a C1-C6 alkyl group.[Aspect 37] The compound according to the Aspect 1, wherein

[0258] Z represents an oxygen atom; and

[0259] R2 represents an ethyl group.[Aspect 38] The compound according to the Aspect 2, wherein

[0260] Z represents an oxygen atom; and

[0261] R2 represents an ethyl group.[Aspect 39] The compound according to the Aspect 3, wherein

[0262] Z represents an oxygen atom; and

[0263] R2 represents an ethyl group.[Aspect 40] The compound according to the Aspect 4, wherein

[0264] Z represents an oxygen atom; and

[0265] R2 represents an ethyl group.[Aspect 41] The compound according to the Aspect 5, wherein

[0266] Z represents an oxygen atom; and

[0267] R2 represents an ethyl group.[Aspect 42] The compound according to the Aspect 6, wherein

[0268] Z represents an oxygen atom; and

[0269] R2 represents an ethyl group.[Aspect 43] The compound according to the Aspect 7, wherein

[0270] Z represents an oxygen atom; and

[0271] R2 represents an ethyl group.[Aspect 44] The compound according to the Aspect 8, wherein

[0272] Z represents an oxygen atom; and

[0273] R2 represents an ethyl group.[Aspect 45] The compound according to the Aspect 9, wherein

[0274] Z represents an oxygen atom; and

[0275] R2 represents an ethyl group.[Aspect 46] The compound according to the Aspect 10, wherein

[0276] Z represents an oxygen atom; and

[0277] R2 represents an ethyl group.[Aspect 47] The compound according to the Aspect 11, wherein

[0278] Z represents an oxygen atom; and

[0279] R2 represents an ethyl group.[Aspect 48] The compound according to the Aspect 12, wherein

[0280] Z represents an oxygen atom; and

[0281] R2 represents an ethyl group.[Aspect 49] The compound according to the Aspect 13, wherein

[0282] Z represents an oxygen atom; and

[0283] R2 represents an ethyl group.[Aspect 50] The compound according to the Aspect 14, wherein

[0284] Z represents an oxygen atom; and

[0285] R2 represents an ethyl group.[Aspect 51] The compound according to the Aspect 15, wherein

[0286] Z represents an oxygen atom; and

[0287] R2 represents an ethyl group.[Aspect 52] The compound according to the Aspect 16, wherein

[0288] Z represents an oxygen atom; and

[0289] R2 represents an ethyl group.[Aspect 53] The compound according to the Aspect 17, wherein

[0290] Z represents an oxygen atom; and

[0291] R2 represents an ethyl group.[Aspect 54] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0292] the combination of A1, A2, A3, A4, and A5 represents:

[0293] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[0294] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or

[0295] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[0296] R4a represents a hydrogen atom;

[0297] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0298] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom;

[0299] provided that in the combinations of A1, A2, A3, A4, and A5:

[0300] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[0301] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[0302] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and

[0303] a combination wherein A1, A2, A4, and A5 each represent CH, and A3 represents a nitrogen atom are excluded.[Aspect 55] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0304] the combination of A1, A2, A3, A4, and A5 represents:

[0305] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[0306] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[0307] R4a represents a hydrogen atom; and

[0308] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0309] R4e represents a halogen atom or a hydrogen atom;

[0310] provided that in the combinations of A1, A2, A3, A4, and A5:

[0311] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[0312] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[0313] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and

[0314] a combination wherein A1, A2, A4, and A5 each represent CH, and A3 represents a nitrogen atom are excluded.[Aspect 56] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0315] A1 represents CR4a;

[0316] A2 represents CR4b;

[0317] A3 represents CR4c;

[0318] A4 represents a nitrogen atom or CR4d;

[0319] A5 represents CR4e;

[0320] R4a represents a hydrogen atom;

[0321] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0322] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that in the combinations of A1, A2, A3, A4, and A5:

[0323] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and

[0324] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom are excluded.[Aspect 57] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0325] A1 represents CR4a;

[0326] A2 represents CR4b;

[0327] A3 represents CR4c;

[0328] A4 represents a nitrogen atom or CR4d;

[0329] A5 represents CR4e;

[0330] R4a represents a hydrogen atom;

[0331] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0332] R4e represents a halogen atom or a hydrogen atom;

[0333] provided that in the combinations of A1, A2, A3, A4, and A5:

[0334] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and

[0335] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom are excluded.[Aspect 58] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0336] A1 represents CR4a;

[0337] A2 represents CR4b;

[0338] A3 represents CR4c;

[0339] A4 represents CR4d;

[0340] A5 represents CR4e;

[0341] R4a represents a hydrogen atom;

[0342] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0343] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect 59] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0344] A1 represents CR4a;

[0345] A2 represents CR4b;

[0346] A3 represents CR4c;

[0347] A4 represents CR4d;

[0348] A5 represents CR4e;

[0349] R4a represents a hydrogen atom;

[0350] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; and

[0351] the combination of R4b, R4c, and R4d represents:

[0352] a combination wherein

[0353] R4b represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[0354] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom or a hydrogen atom; or

[0355] a combination wherein

[0356] R4b represents a hydrogen atom;

[0357] R4c represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[0358] R4d represents a hydrogen atom.[Aspect 60] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0359] A1 represents CR4a;

[0360] A2 represents CR4b;

[0361] A3 represents CR4c;

[0362] A4 represents CR4d;

[0363] A5 represents CR4e;

[0364] R4a represents a hydrogen atom;

[0365] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0366] R4e represents a halogen atom or a hydrogen atom; provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect 61] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0367] A1 represents CR4a;

[0368] A2 represents CR4b;

[0369] A3 represents CR4c;

[0370] A4 represents CR4d;

[0371] A5 represents CR4e;

[0372] R4a represents a hydrogen atom;

[0373] R4e represents a halogen atom or a hydrogen atom; and

[0374] the combination of R4b, R4c, and R4d represents:

[0375] a combination wherein

[0376] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0377] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; or

[0378] a combination wherein

[0379] R4b represents a hydrogen atom;

[0380] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0381] R4d represents a hydrogen atom.[Aspect 62] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0382] A1 represents CR4a;

[0383] A2 represents CR4b;

[0384] A3 represents CR4c;

[0385] A4 represents CR4d;

[0386] A5 represents CR4e;

[0387] R4a represents a hydrogen atom;

[0388] R4e represents a halogen atom or a hydrogen atom; and

[0389] the combination of R4b, R4c, and R4d represents:

[0390] a combination wherein

[0391] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0392] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0393] R4d represents a hydrogen atom;

[0394] a combination wherein

[0395] R4b represents a C1-C6 alkyl group optionally

[0396] substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0397] R4c represents a hydrogen atom; and

[0398] R4d represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0399] a combination wherein

[0400] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0401] R4c and R4d each represent a hydrogen atom; or

[0402] a combination wherein

[0403] R4b represents a hydrogen atom;

[0404] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0405] R4d represents a hydrogen atom.[Aspect 63] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0406] A1 represents CR4a;

[0407] A2 represents CR4b;

[0408] A3 represents CR4c;

[0409] A4 represents CR4d;

[0410] A5 represents CR4e;

[0411] R4a represents a hydrogen atom;

[0412] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0413] R4e represents a halogen atom or a hydrogen atom;

[0414] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect 64] The compound according to any one of the Aspects 1 to 53 or the Present compound N, wherein

[0415] A1 represents CR4a;

[0416] A2 represents CR4b;

[0417] A3 represents CR4c;

[0418] A4 represents CR4d;

[0419] A5 represents CR4e;

[0420] R4a represents a hydrogen atom;

[0421] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0422] R4e represents a hydrogen atom;

[0423] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.

[0424] [Aspect A1] A compound represented by formula (IA)

[0425] [wherein R1A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent (s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent (s) selected from Group U, a phenyl group optionally substituted with one or more substituent (s) selected from Group V, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, C(O) R51, C(O) OR51, or C(O) NR51R52 and the other symbols are the same as defined in [1]].[Aspect A2] The compound according to the Aspect A1, wherein R1A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W.[Aspect A3] The compound according to the Aspect A1, wherein R1A represents a C1-C6 alkyl group.[Aspect A4] The compound according to the Aspect A1, wherein

[0426] the combination of G1, G2, G3, and G4 represents:

[0427] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3a;

[0428] a combination wherein G1 represents a nitrogen atom, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0429] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0430] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3a;

[0431] R3a, R3c, and R3d each represent a hydrogen atom; and

[0432] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A5] The compound according to the Aspect A1, wherein

[0433] G1 represents CR3a;

[0434] G2 represents CR3b;

[0435] G3 represents CR3c;

[0436] G4 represents a nitrogen atom or CR3d;

[0437] R3a, R3c, and R3d each represent a hydrogen atom; and

[0438] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A6] The compound according to the Aspect A1, wherein

[0439] G1 represents CR3a;

[0440] G2 represents CR3b;

[0441] G3 represents CR3c;

[0442] G4 represents a nitrogen atom or CR3d;

[0443] R3a, R3c, and R3d each represent a hydrogen atom; and

[0444] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A7] The compound according to the Aspect A1, wherein

[0445] G1 represents CR3a;

[0446] G2 represents CR3b;

[0447] G3 represents CR3c;

[0448] G4 represents CR3d;

[0449] R3a, R3c, and R3d each represent a hydrogen atom; and

[0450] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A8] The compound according to the Aspect A1, wherein

[0451] G1 represents CR3a;

[0452] G2 represents CR3b;

[0453] G3 represents CR3c;

[0454] G4 represents CR3d;

[0455] R3a, R3c, and R3d each represent a hydrogen atom; and

[0456] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A9] The compound according to the Aspect A2, wherein

[0457] the combination of G1, G2, G3, and G4 represents:

[0458] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3a;

[0459] a combination wherein G1 represents a nitrogen atom, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0460] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0461] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3a;

[0462] R3a, R3c, and R3d each represent a hydrogen atom; and

[0463] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A10] The compound according to the Aspect A3, wherein

[0464] the combination of G1, G2, G3, and G4 represents:

[0465] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3a;

[0466] a combination wherein G1 represents a nitrogen atom,

[0467] G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[0468] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[0469] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3d;

[0470] R3a, R3c, and R3d each represent a hydrogen atom; and

[0471] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A11] The compound according to the Aspect A2, wherein

[0472] G1 represents CR3a;

[0473] G2 represents CR3b;

[0474] G3 represents CR3c;

[0475] G4 represents a nitrogen atom or CR3d;

[0476] R3a, R3c, and R3d each represent a hydrogen atom; and

[0477] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A12] The compound according to the Aspect A3, wherein

[0478] G1 represents CR3a;

[0479] G2 represents CR3b;

[0480] G3 represents CR3c;

[0481] G4 represents a nitrogen atom or CR3d;

[0482] R3a, R3c, and R3d each represent a hydrogen atom; and

[0483] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A13] The compound according to the Aspect A2, wherein

[0484] G1 represents CR3a;

[0485] G2 represents CR3b;

[0486] G3 represents CR3c;

[0487] G4 represents a nitrogen atom or CR3d;

[0488] R3a, R3c, and R3d each represent a hydrogen atom; and

[0489] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A14] The compound according to the Aspect A3, wherein

[0490] G1 represents CR3a;

[0491] G2 represents CR3b;

[0492] G3 represents CR3c;

[0493] G4 represents a nitrogen atom or CR3d;

[0494] R3a, R3c, and R3d each represent a hydrogen atom; and

[0495] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A15] The compound according to the Aspect A2, wherein

[0496] G1 represents CR3a;

[0497] G2 represents CR3b;

[0498] G3 represents CR3c;

[0499] G4 represents CR3d;

[0500] R3a, R3c, and R3d each represent a hydrogen atom; and

[0501] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A16] The compound according to the Aspect A3, wherein

[0502] G1 represents CR3a;

[0503] G2 represents CR3b;

[0504] G3 represents CR3c;

[0505] G4 represents CR3d;

[0506] R3a, R3c, and R3d each represent a hydrogen atom; and

[0507] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect A17] The compound according to the Aspect A2, wherein

[0508] G1 represents CR3a;

[0509] G2 represents CR3b;

[0510] G3 represents CR3c;

[0511] G4 represents CR3d;

[0512] R3a, R3c, and R3d each represent a hydrogen atom; and

[0513] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A18] The compound according to the Aspect A3, wherein

[0514] G1 represents CR3a;

[0515] G2 represents CR3b;

[0516] G3 represents CR3c;

[0517] G4 represents CR3d;

[0518] R3a, R3c, and R3d each represent a hydrogen atom; and

[0519] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect A19] The compound according to the Aspect A1, wherein

[0520] Z represents an oxygen atom; and

[0521] R2 represents a C1-C6 alkyl group.[Aspect A20] The compound according to the Aspect A1, wherein

[0522] Z represents an oxygen atom; and

[0523] R2 represents an ethyl group.[Aspect A21] The compound according to the Aspect A2, wherein

[0524] Z represents an oxygen atom; and

[0525] R2 represents a C1-C6 alkyl group.[Aspect A22] The compound according to the Aspect A3, wherein

[0526] Z represents an oxygen atom; and

[0527] R2 represents a C1-C6 alkyl group.[Aspect A23] The compound according to the Aspect A4, wherein

[0528] Z represents an oxygen atom; and

[0529] R2 represents a C1-C6 alkyl group.[Aspect A24] The compound according to the Aspect A5, wherein

[0530] Z represents an oxygen atom; and

[0531] R2 represents a C1-C6 alkyl group.[Aspect A25] The compound according to the Aspect A6, wherein

[0532] Z represents an oxygen atom; and

[0533] R2 represents a C1-C6 alkyl group.[Aspect A26] The compound according to the Aspect A7, wherein

[0534] Z represents an oxygen atom; and

[0535] R2 represents a C1-C6 alkyl group.[Aspect A27] The compound according to the Aspect A8, wherein

[0536] Z represents an oxygen atom; and

[0537] R2 represents a C1-C6 alkyl group.[Aspect A28] The compound according to the Aspect A9, wherein

[0538] Z represents an oxygen atom; and

[0539] R2 represents a C1-C6 alkyl group.[Aspect A29] The compound according to the Aspect A10, wherein

[0540] Z represents an oxygen atom; and

[0541] R2 represents a C1-C6 alkyl group.[Aspect A30] The compound according to the Aspect A11, wherein

[0542] Z represents an oxygen atom; and

[0543] R2 represents a C1-C6 alkyl group.[Aspect A31] The compound according to the Aspect A12, wherein

[0544] Z represents an oxygen atom; and

[0545] R2 represents a C1-C6 alkyl group.[Aspect A32] The compound according to the Aspect A13, wherein

[0546] Z represents an oxygen atom; and

[0547] R2 represents a C1-C6 alkyl group.[Aspect A33] The compound according to the Aspect A14, wherein

[0548] Z represents an oxygen atom; and

[0549] R2 represents a C1-C6 alkyl group.[Aspect A34] The compound according to the Aspect A15, wherein

[0550] Z represents an oxygen atom; and

[0551] R2 represents a C1-C6 alkyl group.[Aspect A35] The compound according to the Aspect A16, wherein

[0552] Z represents an oxygen atom; and

[0553] R2 represents a C1-C6 alkyl group.[Aspect A36] The compound according to the Aspect A17, wherein

[0554] Z represents an oxygen atom; and

[0555] R2 represents a C1-C6 alkyl group.[Aspect A37] The compound according to the Aspect A18, wherein

[0556] Z represents an oxygen atom; and

[0557] R2 represents a C1-C6 alkyl group.[Aspect A38] The compound according to the Aspect A2, wherein

[0558] Z represents an oxygen atom; and

[0559] R2 represents an ethyl group.[Aspect A39] The compound according to the Aspect A3, wherein

[0560] Z represents an oxygen atom; and

[0561] R2 represents an ethyl group.[Aspect A40] The compound according to the Aspect A4, wherein

[0562] Z represents an oxygen atom; and

[0563] R2 represents an ethyl group.[Aspect A41] The compound according to the Aspect A5, wherein

[0564] Z represents an oxygen atom; and

[0565] R2 represents an ethyl group.[Aspect A42] The compound according to the Aspect A6, wherein

[0566] Z represents an oxygen atom; and

[0567] R2 represents an ethyl group.[Aspect A43] The compound according to the Aspect A7, wherein

[0568] Z represents an oxygen atom; and

[0569] R2 represents an ethyl group.[Aspect A44] The compound according to the Aspect A8, wherein

[0570] Z represents an oxygen atom; and

[0571] R2 represents an ethyl group.[Aspect A45] The compound according to the Aspect A9, wherein

[0572] Z represents an oxygen atom; and

[0573] R2 represents an ethyl group.[Aspect A46] The compound according to the Aspect A10, wherein

[0574] Z represents an oxygen atom; and

[0575] R2 represents an ethyl group.[Aspect A47] The compound according to the Aspect A11, wherein

[0576] Z represents an oxygen atom; and

[0577] R2 represents an ethyl group.[Aspect A48] The compound according to the Aspect A12, wherein

[0578] Z represents an oxygen atom; and

[0579] R2 represents an ethyl group.[Aspect A49] The compound according to the Aspect A13, wherein

[0580] Z represents an oxygen atom; and

[0581] R2 represents an ethyl group.[Aspect A50] The compound according to the Aspect A14, wherein

[0582] Z represents an oxygen atom; and

[0583] R2 represents an ethyl group.[Aspect A51] The compound according to the Aspect A15, wherein

[0584] Z represents an oxygen atom; and

[0585] R2 represents an ethyl group.[Aspect A52] The compound according to the Aspect A16, wherein

[0586] Z represents an oxygen atom; and

[0587] R2 represents an ethyl group.[Aspect A53] The compound according to the Aspect A17, wherein

[0588] Z represents an oxygen atom; and

[0589] R2 represents an ethyl group.[Aspect A54] The compound according to the Aspect A18, wherein

[0590] Z represents an oxygen atom; and

[0591] R2 represents an ethyl group.[Aspect A55] The compound according to any one of the Aspects A1 to A54, wherein

[0592] the combination of A1, A2, A3, A4, and A5 represents:

[0593] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4a, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[0594] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or

[0595] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[0596] R4a represents a hydrogen atom;

[0597] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0598] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom;

[0599] provided that in the combinations of A1, A2, A3, A4, and A5:

[0600] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[0601] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[0602] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and

[0603] a combination wherein A1, A2, A4, and A5 each represent CH, and A3 represents a nitrogen atom are excluded.[Aspect A56] The compound according to any one of the Aspects A1 to A54, wherein

[0604] the combination of A1, A2, A3, A4, and A5 represents:

[0605] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[0606] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or

[0607] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[0608] R4a represents a hydrogen atom;

[0609] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0610] R4e represents a halogen atom or a hydrogen atom;

[0611] provided that in the combinations of A1, A2, A3, A4, and A5:

[0612] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[0613] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[0614] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and a combination wherein A1, A2, A4, and A5 each

[0615] represent CH, and A3 represents a nitrogen atom are excluded.[Aspect A57] The compound according to any one of the Aspects A1 to A54, wherein

[0616] A1 represents CR4a;

[0617] A2 represents CR4b;

[0618] A3 represents CR4c;

[0619] A4 represents a nitrogen atom or CR4d;

[0620] A5 represents CR4e;

[0621] R4a represents a hydrogen atom;

[0622] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0623] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that in the combinations of A1, A2, A3, A4, and A5:

[0624] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and a combination wherein A1, A2, A3, and A5 each

[0625] represent CH, and A4 represents a nitrogen atom are excluded.[Aspect A58] The compound according to any one of the Aspects A1 to A54, wherein

[0626] A1 represents CR4a;

[0627] A2 represents CR4b;

[0628] A3 represents CR4c;

[0629] A4 represents a nitrogen atom or CR4d;

[0630] A5 represents CR4e;

[0631] R4a represents a hydrogen atom;

[0632] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0633] R4e represents a halogen atom or a hydrogen atom; provided that in the combinations of A1, A2, A3, A4, and A5:

[0634] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and

[0635] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom are excluded.[Aspect A59] The compound according to any one of the Aspects A1 to A54, wherein

[0636] A1 represents CR4a;

[0637] A2 represents CR4b;

[0638] A3 represents CR4c;

[0639] A4 represents CR4d;

[0640] A5 represents CR4e;

[0641] R4a represents a hydrogen atom;

[0642] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[0643] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect A60] The compound according to any one of the Aspects A1 to A54, wherein

[0644] A1 represents CR4a;

[0645] A2 represents CR4b;

[0646] A3 represents CR4c;

[0647] A4 represents CR4d;

[0648] A5 represents CR4e;

[0649] R4a represents a hydrogen atom;

[0650] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; and

[0651] the combination of R4b, R4c, and R4d represents:

[0652] a combination wherein

[0653] R4b represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[0654] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom or a hydrogen atom; or

[0655] a combination wherein

[0656] R4b represents a hydrogen atom;

[0657] R4c represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[0658] R4d represents a hydrogen atom.[Aspect A61] The compound according to any one of the Aspects A1 to A54, wherein

[0659] A1 represents CR4a;

[0660] A2 represents CR4b;

[0661] A3 represents CR4c;

[0662] A4 represents CR4d;

[0663] A5 represents CR4e;

[0664] R4a represents a hydrogen atom;

[0665] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[0666] R4e represents a halogen atom or a hydrogen atom;

[0667] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect A62] The compound according to any one of the Aspects A1 to A54, wherein

[0668] A1 represents CR4a;

[0669] A2 represents CR4b;

[0670] A3 represents CR4c;

[0671] A4 represents CR4d;

[0672] A5 represents CR4e;

[0673] R4a represents a hydrogen atom;

[0674] R4e represents a halogen atom or a hydrogen atom; and

[0675] the combination of R4b, R4c, and R4d represents:

[0676] a combination wherein

[0677] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0678] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; or

[0679] a combination wherein

[0680] R4b represents a hydrogen atom;

[0681] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0682] R4d represents a hydrogen atom.[Aspect A63] The compound according to any one of the Aspects A1 to A54, wherein

[0683] A1 represents CR4a;

[0684] A2 represents CR4b;

[0685] A3 represents CR4c;

[0686] A4 represents CR4d;

[0687] A5 represents CR4e;

[0688] R4a represents a hydrogen atom;

[0689] R4e represents a halogen atom or a hydrogen atom; and

[0690] the combination of R4b, R4c, and R4d represents:

[0691] a combination wherein

[0692] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0693] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0694] R4d represents a hydrogen atom;

[0695] a combination wherein

[0696] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0697] R4c represents a hydrogen atom; and

[0698] R4d represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[0699] a combination wherein

[0700] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0701] R4c and R4d each represent a hydrogen atom; or

[0702] a combination wherein

[0703] R4b represents a hydrogen atom;

[0704] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[0705] R4d represents a hydrogen atom.[Aspect A64] The compound according to any one of the Aspects A1 to A54, wherein

[0706] A1 represents CR4a;

[0707] A2 represents CR4b;

[0708] A3 represents CR4c;

[0709] A4 represents CR4d;

[0710] A5 represents CR4e;

[0711] R4a represents a hydrogen atom;

[0712] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0713] R4e represents a halogen atom or a hydrogen atom;

[0714] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect A65] The compound according to any one of the Aspects A1 to A54, wherein

[0715] A1 represents CR4a;

[0716] A2 represents CR4b;

[0717] A3 represents CR4c;

[0718] A4 represents CR4d;

[0719] A5 represents CR4e;

[0720] R4a represents a hydrogen atom;

[0721] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0722] R4e represents a hydrogen atom;

[0723] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.

[0724] [Aspect B1] A compound represented by formula (IB)

[0725] [wherein the symbols are the same as defined in [2]], [Aspect B2] The compound according to the Aspect B1, wherein

[0726] R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0727] R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, or a hydrogen atom.[Aspect B3] The compound according to the Aspect B1, wherein

[0728] R41, R42, and R45 are identical to or different from each other, and each represent a C1-C6 alkyl group or a hydrogen atom.[Aspect B4] The compound according to the Aspect B1, wherein

[0729] G1 represents CR3a;

[0730] G2 represents CR3b;

[0731] G3 represents CR3c;

[0732] G4 represents a nitrogen atom or CR3a;

[0733] R3a, R3c, and R3d each represent a hydrogen atom; and

[0734] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B5] The compound according to the Aspect B1, wherein

[0735] G1 represents CR3a;

[0736] G2 represents CR3b;

[0737] G3 represents CR3c;

[0738] G4 represents a nitrogen atom or CR3d;

[0739] R3a, R3c, and R3d each represent a hydrogen atom; and

[0740] R3b represents a halogen atom.[Aspect B6] The compound according to the Aspect B1, wherein

[0741] G1 represents CR3a;

[0742] G2 represents CR3b;

[0743] G3 represents CR3c;

[0744] G4 represents CR3a;

[0745] R3a, R3c, and R3d each represent a hydrogen atom; and

[0746] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B7] The compound according to the Aspect B1, wherein

[0747] G1 represents CR3a;

[0748] G2 represents CR3b;

[0749] G3 represents CR3c;

[0750] G4 represents CR3d;

[0751] R3a, R3c, and R3d each represent a hydrogen atom; and

[0752] R3b represents a halogen atom.[Aspect B8] The compound according to the Aspect B2, wherein

[0753] G1 represents CR3a;

[0754] G2 represents CR3b;

[0755] G3 represents CR3c;

[0756] G4 represents a nitrogen atom or CR3a;

[0757] R3a, R3c, and R3d each represent a hydrogen atom; and

[0758] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B9] The compound according to the Aspect B3, wherein

[0759] G1 represents CR3a;

[0760] G2 represents CR3b;

[0761] G3 represents CR3c;

[0762] G4 represents a nitrogen atom or CR3a;

[0763] R3a, R3c, and R3d each represent a hydrogen atom; and

[0764] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B10] The compound according to the Aspect B2, wherein

[0765] G1 represents CR3a;

[0766] G2 represents CR3b;

[0767] G3 represents CR3c;

[0768] G4 represents a nitrogen atom or CR3a;

[0769] R3a, R3c, and R3d each represent a hydrogen atom; and

[0770] R3b represents a halogen atom.[Aspect B11] The compound according to the Aspect B3, wherein

[0771] G1 represents CR3a;

[0772] G2 represents CR3b;

[0773] G3 represents CR3c;

[0774] G4 represents a nitrogen atom or CR3a;

[0775] R3a, R3c, and R3d each represent a hydrogen atom; and

[0776] R3b represents a halogen atom.[Aspect B12] The compound according to the Aspect B2, wherein

[0777] G1 represents CR3a;

[0778] G2 represents CR3b;

[0779] G3 represents CR3c;

[0780] G4 represents CR3d;

[0781] R3a, R3c, and R3d each represent a hydrogen atom; and

[0782] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B13] The compound according to the Aspect B3, wherein

[0783] G1 represents CR3a;

[0784] G2 represents CR3b;

[0785] G3 represents CR3c;

[0786] G4 represents CR3d;

[0787] R3a, R3c, and R3d each represent a hydrogen atom; and

[0788] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B14] The compound according to the Aspect B2, wherein

[0789] G1 represents CR3a;

[0790] G2 represents CR3b;

[0791] G3 represents CR3c;

[0792] G4 represents CR3a;

[0793] R3a, R3c, and R3d each represent a hydrogen atom; and

[0794] R3b represents a halogen atom.[Aspect B15] The compound according to the Aspect B3, wherein

[0795] G1 represents CR3a;

[0796] G2 represents CR3b;

[0797] G3 represents CR3c;

[0798] G4 represents CR3d;

[0799] R3a, R3c, and R3d each represent a hydrogen atom; and

[0800] R3b represents a halogen atom.[Aspect B16] The compound according to the Aspect B1, wherein

[0801] Z represents an oxygen atom; and

[0802] R2 represents a C1-C6 alkyl group.[Aspect B17] The compound according to the Aspect B1, wherein

[0803] Z represents an oxygen atom; and

[0804] R2 represents an ethyl group.[Aspect B18] The compound according to the Aspect B2, wherein

[0805] Z represents an oxygen atom; and

[0806] R2 represents a C1-C6 alkyl group.[Aspect B19] The compound according to the Aspect B3, wherein

[0807] Z represents an oxygen atom; and

[0808] R2 represents a C1-C6 alkyl group.[Aspect B20] The compound according to the Aspect B4, wherein

[0809] Z represents an oxygen atom; and

[0810] R2 represents a C1-C6 alkyl group.[Aspect B21] The compound according to the Aspect B5, wherein

[0811] Z represents an oxygen atom; and

[0812] R2 represents a C1-C6 alkyl group.[Aspect B22] The compound according to the Aspect B6, wherein

[0813] Z represents an oxygen atom; and

[0814] R2 represents a C1-C6 alkyl group.[Aspect B23] The compound according to the Aspect B7, wherein

[0815] Z represents an oxygen atom; and

[0816] R2 represents a C1-C6 alkyl group.[Aspect B24] The compound according to the Aspect B8, wherein

[0817] Z represents an oxygen atom; and

[0818] R2 represents a C1-C6 alkyl group.[Aspect B25] The compound according to the Aspect B9, wherein

[0819] Z represents an oxygen atom; and

[0820] R2 represents a C1-C6 alkyl group.[Aspect B26] The compound according to the Aspect B10, wherein

[0821] Z represents an oxygen atom; and

[0822] R2 represents a C1-C6 alkyl group.[Aspect B27] The compound according to the Aspect B11, wherein

[0823] Z represents an oxygen atom; and

[0824] R2 represents a C1-C6 alkyl group.[Aspect B28] The compound according to the Aspect B12, wherein

[0825] Z represents an oxygen atom; and

[0826] R2 represents a C1-C6 alkyl group.[Aspect B29] The compound according to the Aspect B13, wherein

[0827] Z represents an oxygen atom; and

[0828] R2 represents a C1-C6 alkyl group.[Aspect B30] The compound according to the Aspect B14, wherein

[0829] Z represents an oxygen atom; and

[0830] R2 represents a C1-C6 alkyl group.[Aspect B31] The compound according to the Aspect B15, wherein

[0831] Z represents an oxygen atom; and

[0832] R2 represents a C1-C6 alkyl group.[Aspect B32] The compound according to the Aspect B2, wherein

[0833] Z represents an oxygen atom; and

[0834] R2 represents an ethyl group.[Aspect B33] The compound according to the Aspect B3, wherein

[0835] Z represents an oxygen atom; and

[0836] R2 represents an ethyl group.[Aspect B34] The compound according to the Aspect B4, wherein

[0837] Z represents an oxygen atom; and

[0838] R2 represents an ethyl group.[Aspect B35] The compound according to the Aspect B5, wherein

[0839] Z represents an oxygen atom; and

[0840] R2 represents an ethyl group.[Aspect B36] The compound according to the Aspect B6, wherein

[0841] Z represents an oxygen atom; and

[0842] R2 represents an ethyl group.[Aspect B37] The compound according to the Aspect B7, wherein

[0843] Z represents an oxygen atom; and

[0844] R2 represents an ethyl group.[Aspect B38] The compound according to the Aspect B8, wherein

[0845] Z represents an oxygen atom; and

[0846] R2 represents an ethyl group.[Aspect B39] The compound according to the Aspect B9, wherein

[0847] Z represents an oxygen atom; and

[0848] R2 represents an ethyl group.[Aspect B40] The compound according to the Aspect B10, wherein

[0849] Z represents an oxygen atom; and

[0850] R2 represents an ethyl group.[Aspect B41] The compound according to the Aspect B11, wherein

[0851] Z represents an oxygen atom; and

[0852] R2 represents an ethyl group.[Aspect B42] The compound according to the Aspect B12, wherein

[0853] Z represents an oxygen atom; and

[0854] R2 represents an ethyl group.[Aspect B43] The compound according to the Aspect B13, wherein

[0855] Z represents an oxygen atom; and

[0856] R2 represents an ethyl group.[Aspect B44] The compound according to the Aspect B14, wherein

[0857] Z represents an oxygen atom; and

[0858] R2 represents an ethyl group.[Aspect B45] The compound according to the Aspect B15, wherein

[0859] Z represents an oxygen atom; and

[0860] R2 represents an ethyl group.[Aspect B46] The compound according to any one of the Aspects B1 to B45, wherein

[0861] the combination of A1, A2, A3, and A4 represents:

[0862] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4a, and A4 represents a nitrogen atom or CR4d;

[0863] a combination wherein A1 represents CR4a, A2 represents a nitrogen atom, A3 represents CR4a, and A4 represents CR4d; or

[0864] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, and A4 represents CR4d;

[0865] R4a and R4d each represent a hydrogen atom; and

[0866] R4b and R4c are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, OR44, a halogen atom, or a hydrogen atom;

[0867] provided that in the combinations of A1, A2, A3, and A4:

[0868] a combination wherein A1, A2, A3, and A4 each represent CH;

[0869] a combination wherein A1, A2, and A3 each represent CH, and A4 represents a nitrogen atom;

[0870] a combination wherein A1, A2, and A4 each represent CH, and A3 represents a nitrogen atom; and

[0871] a combination wherein A1, A3, and A4 each represent CH, and A2 represents a nitrogen atom are excluded.[Aspect B47] The compound according to any one of the Aspects B1 to B45, wherein

[0872] the combination of A1, A2, A3, and A4 represents:

[0873] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, and A4 represents a nitrogen atom or CR4d;

[0874] a combination wherein A1 represents CR4a, A2 represents a nitrogen atom, A3 represents CR4c, and A4 represents CR4d; or

[0875] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, and A4 represents CR4d;

[0876] R4a and R4d each represent a hydrogen atom; and

[0877] R4b and R4c are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), or a hydrogen atom; provided that in the combinations of A1, A2, A3, and A4:

[0878] a combination wherein A1, A2, A3, and A4 each represent CH;

[0879] a combination wherein A1, A2, and A3 each represent CH, and A4 represents a nitrogen atom;

[0880] a combination wherein A1, A2, and A4 each represent CH, and A3 represents a nitrogen atom; and

[0881] a combination wherein A1, A3, and A4 each represent CH, and A2 represents a nitrogen atom are excluded.[Aspect B48] The compound according to any one of the Aspects B1 to B45, wherein

[0882] A1 represents CR4a;

[0883] A2 represents CR4b;

[0884] A3 represents CR4c;

[0885] A4 represents CR4d;

[0886] R4a and R4d each represent a hydrogen atom; and

[0887] R4b and R4c are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, OR44, a halogen atom, or a hydrogen atom;

[0888] provided that a combination wherein R4b and R4c each represent a hydrogen atom is excluded.[Aspect B49] The compound according to any one of the Aspects B1 to B45, wherein

[0889] A1 represents CR4a;

[0890] A2 represents CR4b;

[0891] A3 represents CR4c;

[0892] A4 represents CR4d;

[0893] R4a and R4d each represent a hydrogen atom; and

[0894] R4b and R4c are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), or a hydrogen atom;

[0895] provided that a combination wherein R4b and R4c each represent a hydrogen atom is excluded.[Aspect B50] A compound represented by formula (IB)

[0896] [wherein the symbols are the same as defined in [1]].[Aspect B51] The compound according to the Aspect B50, wherein

[0897] R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[0898] R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent (s) selected from Group X, or a hydrogen atom.[Aspect B52] The compound according to the Aspect B50, wherein

[0899] R41,R42 and R45 are identical to or different from each other, and each represent a C1-C6 alkyl group or a hydrogen atom.[Aspect B53] The compound according to the Aspect B50, wherein

[0900] G1 represents CR3a;

[0901] G2 represents CR3b;

[0902] G3 represents CR3c;

[0903] G4 represents a nitrogen atom or CR3d;

[0904] R3a, R3c, and R3d each represent a hydrogen atom; and

[0905] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B54] The compound according to the Aspect B50, wherein

[0906] G1 represents CR3a;

[0907] G2 represents CR3b;

[0908] G3 represents CR3c;

[0909] G4 represents a nitrogen atom or CR3a;

[0910] R3a, R3c, and R3d each represent a hydrogen atom; and

[0911] R3b represents a halogen atom.[Aspect B55] The compound according to the Aspect B50, wherein

[0912] G1 represents CR3a;

[0913] G2 represents CR3b;

[0914] G3 represents CR3c;

[0915] G4 represents CR3d;

[0916] R3a, R3c, and R3d each represent a hydrogen atom; and

[0917] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B56] The compound according to the Aspect B50, wherein

[0918] G1 represents CR3a;

[0919] G2 represents CR3b;

[0920] G3 represents CR3c;

[0921] G4 represents CR3d;

[0922] R3a, R3c, and R3d each represent a hydrogen atom; and

[0923] R3b represents a halogen atom.[Aspect B57] The compound according to the Aspect B51, wherein

[0924] G1 represents CR3a;

[0925] G2 represents CR3b;

[0926] G3 represents CR3c;

[0927] G4 represents a nitrogen atom or CR3d;

[0928] R3a, R3c, and R3d each represent a hydrogen atom; and

[0929] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B58] The compound according to the Aspect B52, wherein

[0930] G1 represents CR3a;

[0931] G2 represents CR3b;

[0932] G3 represents CR3c;

[0933] G4 represents a nitrogen atom or CR3d;

[0934] R3a, R3c, and R3d each represent a hydrogen atom; and

[0935] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B59] The compound according to the Aspect B51, wherein

[0936] G1 represents CR3a;

[0937] G2 represents CR3b;

[0938] G3 represents CR3c;

[0939] G4 represents a nitrogen atom or CR3a;

[0940] R3a, R3c, and R3d each represent a hydrogen atom; and

[0941] R3b represents a halogen atom.[Aspect B60] The compound according to the Aspect B52, wherein

[0942] G1 represents CR3a;

[0943] G2 represents CR3b;

[0944] G3 represents CR3c;

[0945] G4 represents a nitrogen atom or CR3d;

[0946] R3a, R3c, and R3d each represent a hydrogen atom; and

[0947] R3b represents a halogen atom.[Aspect B61] The compound according to the Aspect B51, wherein

[0948] G1 represents CR3a;

[0949] G2 represents CR3b;

[0950] G3 represents CR3c;

[0951] G4 represents CR3d;

[0952] R3a, R3c, and R3d each represent a hydrogen atom; and

[0953] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B62] The compound according to the Aspect B52, wherein

[0954] G1 represents CR3a;

[0955] G2 represents CR3b;

[0956] G3 represents CR3c;

[0957] G4 represents CR3a;

[0958] R3a, R3c, and R3d each represent a hydrogen atom; and

[0959] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, or a hydrogen atom.[Aspect B63] The compound according to the Aspect B51, wherein

[0960] G1 represents CR3a;

[0961] G2 represents CR3b;

[0962] G3 represents CR3c;

[0963] G4 represents CR3d;

[0964] R3a, R3c, and R3d each represent a hydrogen atom; and

[0965] R3b represents a halogen atom.[Aspect B64] The compound according to the Aspect B52, wherein

[0966] G1 represents CR3a;

[0967] G2 represents CR3b;

[0968] G3 represents CR3c;

[0969] G4 represents CR3d;

[0970] R3a, R3c, and R3d each represent a hydrogen atom; and

[0971] R3b represents a halogen atom.[Aspect B65] The compound according to the Aspect B50, wherein

[0972] Z represents an oxygen atom; and

[0973] R2 represents a C1-C6 alkyl group.[Aspect B66] The compound according to the Aspect B50, wherein

[0974] Z represents an oxygen atom; and

[0975] R2 represents an ethyl group.[Aspect B67] The compound according to the Aspect B51, wherein

[0976] Z represents an oxygen atom; and

[0977] R2 represents a C1-C6 alkyl group.[Aspect B68] The compound according to the Aspect B52, wherein

[0978] Z represents an oxygen atom; and

[0979] R2 represents a C1-C6 alkyl group.[Aspect B69] The compound according to the Aspect B53, wherein

[0980] Z represents an oxygen atom; and

[0981] R2 represents a C1-C6 alkyl group.[Aspect B70] The compound according to the Aspect B54, wherein

[0982] Z represents an oxygen atom; and

[0983] R2 represents a C1-C6 alkyl group.[Aspect B71] The compound according to the Aspect B55, wherein

[0984] Z represents an oxygen atom; and

[0985] R2 represents a C1-C6 alkyl group.[Aspect B72] The compound according to the Aspect B56, wherein

[0986] Z represents an oxygen atom; and

[0987] R2 represents a C1-C6 alkyl group.[Aspect B73] The compound according to the Aspect B57, wherein

[0988] Z represents an oxygen atom; and

[0989] R2 represents a C1-C6 alkyl group.[Aspect B74] The compound according to the Aspect B58, wherein

[0990] Z represents an oxygen atom; and

[0991] R2 represents a C1-C6 alkyl group.[Aspect B75] The compound according to the Aspect B59, wherein

[0992] Z represents an oxygen atom; and

[0993] R2 represents a C1-C6 alkyl group.[Aspect B76] The compound according to the Aspect B60, wherein

[0994] Z represents an oxygen atom; and

[0995] R2 represents a C1-C6 alkyl group.[Aspect B77] The compound according to the Aspect B61, wherein

[0996] Z represents an oxygen atom; and

[0997] R2 represents a C1-C6 alkyl group.[Aspect B78] The compound according to the Aspect B62, wherein

[0998] Z represents an oxygen atom; and

[0999] R2 represents a C1-C6 alkyl group.[Aspect B79] The compound according to the Aspect B63, wherein

[1000] Z represents an oxygen atom; and

[1001] R2 represents a C1-C6 alkyl group.[Aspect B80] The compound according to the Aspect B64, wherein

[1002] Z represents an oxygen atom; and

[1003] R2 represents a C1-C6 alkyl group.[Aspect B81] The compound according to the Aspect B51, wherein

[1004] Z represents an oxygen atom; and

[1005] R2 represents an ethyl group.[Aspect B82] The compound according to the Aspect B52, wherein

[1006] Z represents an oxygen atom; and

[1007] R2 represents an ethyl group.[Aspect B83] The compound according to the Aspect B53, wherein

[1008] Z represents an oxygen atom; and

[1009] R2 represents an ethyl group.[Aspect B84] The compound according to the Aspect B54, wherein

[1010] Z represents an oxygen atom; and

[1011] R2 represents an ethyl group.[Aspect B85] The compound according to the Aspect B55, wherein

[1012] Z represents an oxygen atom; and

[1013] R2 represents an ethyl group.[Aspect B86] The compound according to the Aspect B56, wherein

[1014] Z represents an oxygen atom; and

[1015] R2 represents an ethyl group.[Aspect B87] The compound according to the Aspect B57, wherein

[1016] Z represents an oxygen atom; and

[1017] R2 represents an ethyl group.[Aspect B88] The compound according to the Aspect B58, wherein

[1018] Z represents an oxygen atom; and

[1019] R2 represents an ethyl group.[Aspect B89] The compound according to the Aspect B59, wherein

[1020] Z represents an oxygen atom; and

[1021] R2 represents an ethyl group.[Aspect B90] The compound according to the Aspect B60, wherein

[1022] Z represents an oxygen atom; and

[1023] R2 represents an ethyl group.[Aspect B91] The compound according to the Aspect B61, wherein

[1024] Z represents an oxygen atom; and

[1025] R2 represents an ethyl group.[Aspect B92] The compound according to the Aspect B62, wherein

[1026] Z represents an oxygen atom; and

[1027] R2 represents an ethyl group.[Aspect B93] The compound according to the Aspect B63, wherein

[1028] Z represents an oxygen atom; and

[1029] R2 represents an ethyl group.[Aspect B94] The compound according to the Aspect B64, wherein

[1030] Z represents an oxygen atom; and

[1031] R2 represents an ethyl group.[Aspect B95] The compound according to any one of the Aspects B50 to B94, wherein

[1032] the combination of A1, A2, A3, and A4 represents:

[1033] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4a, and A4 represents a nitrogen atom or CR4d;

[1034] a combination wherein A1 represents CR4a, A2 represents a nitrogen atom, A3 represents CR4c, and A4 represents CR4d; or

[1035] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, and A4 represents CR4d;

[1036] R4a and R4d each represent a hydrogen atom; and

[1037] R4b and R4c are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, OR44, a halogen atom, or a hydrogen atom;

[1038] provided that in the combinations of A1, A2, A3, and A4:

[1039] a combination wherein A1, A2, A3, and A4 each represent CH;

[1040] a combination wherein A1, A2, and A3 each represent CH, and A4 represents a nitrogen atom;

[1041] a combination wherein A1, A2, and A4 each represent CH, and A3 represents a nitrogen atom; and

[1042] a combination wherein A1, A3, and A4 each represent CH, and A2 represents a nitrogen atom are excluded.[Aspect B96] The compound according to any one of the Aspects B50 to B94, wherein

[1043] the combination of A1, A2, A3, and A4 represents:

[1044] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, and A4 represents a nitrogen atom or CR4d;

[1045] a combination wherein A1 represents CR4a, A2 represents a nitrogen atom, A3 represents CR4c, and A4 represents CR4d; or

[1046] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, and A4 represents CR4d;

[1047] R4a and R4d each represent a hydrogen atom; and

[1048] R4b and R4c are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), or a hydrogen atom; provided that in the combinations of A1, A2, A3, and A4:

[1049] a combination wherein A1, A2, A3, and A4 each represent CH;

[1050] a combination wherein A1, A2, and A3 each represent CH, and A4 represents a nitrogen atom;

[1051] a combination wherein A1, A2, and A4 each represent CH, and A3 represents a nitrogen atom; and

[1052] a combination wherein A1, A3, and A4 each represent CH, and A2 represents a nitrogen atom are excluded.[Aspect B97] The compound according to any one of the Aspects B50 to B94, wherein

[1053] A1 represents CR4a;

[1054] A2 represents CR4b;

[1055] A3 represents CR4c;

[1056] A4 represents CR4d;

[1057] R4a and R4d each represent a hydrogen atom; and

[1058] R4b and R4c are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, OR44, a halogen atom, or a hydrogen atom;

[1059] provided that a combination wherein R4b and R4c each represent a hydrogen atom is excluded.[Aspect B98] The compound according to any one of the Aspects B50 to B94, wherein

[1060] A1 represents CR4a;

[1061] A2 represents CR4b;

[1062] A3 represents CR4c;

[1063] A4 represents CR4d;

[1064] R4a and R4d each represent a hydrogen atom; and

[1065] R4b and R4c are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), or a hydrogen atom;

[1066] provided that a combination wherein R4b and R4c each represent a hydrogen atom is excluded.

[1067] Aspects of the compound represented by formula (II) (hereinafter also referred to as “Intermediate compound C”) include the following compounds.[Aspect C1] The compound according to the Intermediate compound C, whereinthe combination of G1, G2, G3, and G4 represents:

[1069] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR3a;

[1070] a combination wherein G1 represents a nitrogen atom,

[1071] G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d;

[1072] a combination wherein G1 represents CR3a, G2 represents a nitrogen atom, G3 represents CR3c, and G4 represents CR3d; or

[1073] a combination wherein G1 represents CR3a, G2 represents CR3b, G3 represents a nitrogen atom, and G4 represents CR3d;

[1074] R3a, R3c, and R3d each represent a hydrogen atom; and

[1075] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect C2] The compound according to the Intermediate compound C, wherein

[1076] G1 represents CR3a;

[1077] G2 represents CR3b;

[1078] G3 represents CR3c;

[1079] G4 represents a nitrogen atom or CR3a;

[1080] R3a, R3c, and R3d each represent a hydrogen atom; and

[1081] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect C3] The compound according to the Intermediate compound C, wherein

[1082] G1 represents CR3a;

[1083] G2 represents CR3b;

[1084] G3 represents CR3c;

[1085] G4 represents a nitrogen atom or CR3d;

[1086] R3a, R3c, and R3d each represent a hydrogen atom; and

[1087] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect C4] The compound according to the Intermediate compound C, wherein

[1088] G1 represents CR3a;

[1089] G2 represents CR3b;

[1090] G3 represents CR3c;

[1091] G4 represents CR3d;

[1092] R3a, R3c, and R3d each represent a hydrogen atom; and

[1093] R3b represents a C1-C6 alkyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group {wherein said phenyl group and said pyridyl group are optionally substituted with one or more halogen atom(s)}, a halogen atom, or a hydrogen atom.[Aspect C5] The compound according to the Intermediate compound C, wherein

[1094] G1 represents CR3a;

[1095] G2 represents CR3b;

[1096] G3 represents CR3c;

[1097] G4 represents CR3d;

[1098] R3a, R3c, and R3d each represent a hydrogen atom; and

[1099] R3b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a halogen atom.[Aspect C6] The compound according to the Intermediate compound C, wherein

[1100] Z represents an oxygen atom; and

[1101] R2 represents a C1-C6 alkyl group.[Aspect C7] The compound according to the Intermediate compound C, wherein

[1102] Z represents an oxygen atom; and

[1103] R2 represents an ethyl group.[Aspect C8] The compound according to the Aspect C1, wherein

[1104] Z represents an oxygen atom; and

[1105] R2 represents a C1-C6 alkyl group.[Aspect C9] The compound according to the Aspect C2, wherein

[1106] Z represents an oxygen atom; and

[1107] R2 represents a C1-C6 alkyl group.[Aspect C10] The compound according to the Aspect C3, wherein

[1108] Z represents an oxygen atom; and

[1109] R2 represents a C1-C6 alkyl group.[Aspect C11] The compound according to the Aspect C4, wherein

[1110] Z represents an oxygen atom; and

[1111] R2 represents a C1-C6 alkyl group.[Aspect C12] The compound according to the Aspect C5, wherein

[1112] Z represents an oxygen atom; and

[1113] R2 represents a C1-C6 alkyl group.[Aspect C13] The compound according to the Aspect C1, wherein

[1114] Z represents an oxygen atom; and

[1115] R2 represents an ethyl group.[Aspect C14] The compound according to the Aspect C2, wherein

[1116] Z represents an oxygen atom; and

[1117] R2 represents an ethyl group.[Aspect C15] The compound according to the Aspect C3, wherein

[1118] Z represents an oxygen atom; and

[1119] R2 represents an ethyl group.[Aspect C16] The compound according to the Aspect C4, wherein

[1120] Z represents an oxygen atom; and

[1121] R2 represents an ethyl group.[Aspect C17] The compound according to the Aspect C5, wherein

[1122] Z represents an oxygen atom; and

[1123] R2 represents an ethyl group.[Aspect C18] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1124] the combination of A1, A2, A3, A4, and A5 represents:

[1125] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4a, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[1126] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or

[1127] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[1128] R4a represents a hydrogen atom;

[1129] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[1130] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that in the combinations of A1, A2, A3, A4, and A5:

[1131] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[1132] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[1133] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and

[1134] a combination wherein A1, A2, A4, and A5 each represent CH, and A3 represents a nitrogen atom are excluded.[Aspect C19] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1135] the combination of A1, A2, A3, A4, and A5 represents:

[1136] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents CR4e;

[1137] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR4d, and A5 represents CR4e; or

[1138] a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR4d, and A5 represents a nitrogen atom;

[1139] R4a represents a hydrogen atom;

[1140] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[1141] R4e represents a halogen atom or a hydrogen atom;

[1142] provided that in the combinations of A1, A2, A3, A4, and A5:

[1143] a combination wherein A1, A2, A3, A4, and A5 each represent CH;

[1144] a combination wherein A1, A2, A3, and A4 each represent CH, and A5 represents a nitrogen atom;

[1145] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom; and

[1146] a combination wherein A1, A2, A4, and A5 each represent CH, and A3 represents a nitrogen atom are excluded.[Aspect C20] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1147] A1 represents CR4a;

[1148] A2 represents CR4b;

[1149] A3 represents CR4c;

[1150] A4 represents a nitrogen atom or CR4d;

[1151] A5 represents CR4e;

[1152] R4a represents a hydrogen atom;

[1153] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[1154] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that in the combinations of A1, A2, A3, A4, and A5:

[1155] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and

[1156] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom are excluded.[Aspect C21] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1157] A1 represents CR4a;

[1158] A2 represents CR4b;

[1159] A3 represents CR4c;

[1160] A4 represents a nitrogen atom or CR4d;

[1161] A5 represents CR4e;

[1162] R4a represents a hydrogen atom;

[1163] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[1164] R4e represents a halogen atom or a hydrogen atom;

[1165] provided that in the combinations of A1, A2, A3, A4, and A5:

[1166] a combination wherein A1, A2, A3, A4, and A5 each represent CH; and

[1167] a combination wherein A1, A2, A3, and A5 each represent CH, and A4 represents a nitrogen atom are excluded.[Aspect C22] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1168] A1 represents CR4a;

[1169] A2 represents CR4b;

[1170] A3 represents CR4c;

[1171] A4 represents CR4d;

[1172] A5 represents CR4e;

[1173] R4a represents a hydrogen atom;

[1174] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom, or a hydrogen atom; and

[1175] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect C23] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1176] A1 represents CR4a;

[1177] A2 represents CR4b;

[1178] A3 represents CR4c;

[1179] A4 represents CR4d;

[1180] A5 represents CR4e;

[1181] R4a represents a hydrogen atom;

[1182] R4e represents a C1-C6 alkyl group, a halogen atom, or a hydrogen atom; and

[1183] the combination of R4b, R4c, and R4d represents:

[1184] a combination wherein

[1185] R4b represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[1186] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, a halogen atom or a hydrogen atom; or

[1187] a combination wherein

[1188] R4b represents a hydrogen atom;

[1189] R4c represents a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group {wherein said C1-C6 alkyl group, said C1-C6 alkenyl group, and said C3-C7 cycloalkyl group are optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a cyano group}, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {wherein said phenyl group, said pyridyl group, said pyrimidinyl group, said pyrazolyl group, and said triazolyl group are optionally substituted with one or more substituent(s) selected from Group J}, OR44, S(O)qR41, a cyano group, or a halogen atom; and

[1190] R4d represents a hydrogen atom.[Aspect C24] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1191] A1 represents CR4a;

[1192] A2 represents CR4b;

[1193] A3 represents CR4c;

[1194] A4 represents CR4d;

[1195] A5 represents CR4e;

[1196] R4a represents a hydrogen atom;

[1197] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; and

[1198] R4e represents a halogen atom or a hydrogen atom;

[1199] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect C25] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1200] A1 represents CR4a;

[1201] A2 represents CR4b;

[1202] A3 represents CR4c;

[1203] A4 represents CR4d;

[1204] A5 represents CR4e;

[1205] R4a represents a hydrogen atom;

[1206] R4e represents a halogen atom or a hydrogen atom; and

[1207] the combination of R4b, R4c, and R4d represents:

[1208] a combination wherein

[1209] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[1210] R4c and R4d are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, a halogen atom, or a hydrogen atom; or

[1211] a combination wherein

[1212] R4b represents a hydrogen atom;

[1213] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[1214] R4d represents a hydrogen atom.[Aspect C26] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1215] A1 represents CR4a;

[1216] A2 represents CR4b;

[1217] A3 represents CR4c;

[1218] A4 represents CR4d;

[1219] A5 represents CR4e;

[1220] R4a represents a hydrogen atom;

[1221] R4e represents a halogen atom or a hydrogen atom; and

[1222] the combination of R4b, R4c, and R4d represents: a combination wherein

[1223] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[1224] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[1225] R4d represents a hydrogen atom;

[1226] a combination wherein

[1227] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[1228] R4c represents a hydrogen atom; and

[1229] R4d represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom;

[1230] a combination wherein

[1231] R4b represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[1232] R4c and R4d each represent a hydrogen atom; or

[1233] a combination wherein

[1234] R4b represents a hydrogen atom;

[1235] R4c represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a cyano group, or a halogen atom; and

[1236] R4d represents a hydrogen atom.[Aspect C27] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1237] A1 represents CR4a;

[1238] A2 represents CR4b;

[1239] A3 represents CR4c;

[1240] A4 represents CR4d;

[1241] A5 represents CR4e;

[1242] R4a represents a hydrogen atom;

[1243] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[1244] R4e represents a halogen atom or a hydrogen atom;

[1245] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.[Aspect C28] The compound according to any one of the Aspects C1 to C17 or the Intermediate compound C, wherein

[1246] A1 represents CR4a;

[1247] A2 represents CR4b;

[1248] A3 represents CR4c;

[1249] A4 represents CR4d;

[1250] A5 represents CR4e;

[1251] R4a represents a hydrogen atom;

[1252] R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom; and

[1253] R4e represents a hydrogen atom;

[1254] provided that not all of R4b, R4c, R4d, and R4e represent hydrogen atoms.

[1255] Next, production methods for the Present compounds X are described.Production Method 1

[1256] A compound represented by formula (I-b) (hereinafter referred to as “Compound (I-b)”) or a compound represented by formula (I-c) (hereinafter referred to as “Compound (I-c)”) may be prepared by reacting a compound represented by formula (I-a) (hereinafter referred to as “Compound (I-a)”) with an oxidizing agent.

[1257] [wherein the symbols are the same as defined above.]

[1258] First, a method for producing the Compound (I-b) from the Compound (I-a) is described.

[1259] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter collectively referred to as “halogenated hydrocarbons”); nitriles such as acetonitrile (hereinafter collectively referred to as “nitriles”); alcohols such as methanol and ethanol (hereinafter collectively re erred to as “alcohols”); acetic acid; water; and mixtures of two or more of them.

[1260] Examples of the oxidizing agent to be used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as “mCPBA”), and hydrogen peroxide.

[1261] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be used as needed.

[1262] Examples of the base to be used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used at a ratio of 0.01 to 1 mol relative to 1 mol of the Compound (I-a).

[1263] Examples of the catalyst to be used in the reaction include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used at a ratio of 0.01 to 0.5 mol relative to 1 mol of the Compound (I-a).

[1264] In the reaction, the oxidizing agent is usually used at a ratio of 1 to 1.2 mol relative to 1 mol of the Compound (I-a).

[1265] The reaction temperature is usually within the range of −20 to 80° C. The reaction time is usually within the range of 0.1 to 12 hours(s).

[1266] When the reaction is completed, to the reaction mixture is added water, the resulting mixture is subjected to extraction with organic solvent(s), and the resulting organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen carbonate) as needed. The resulting organic layer is dried and / or concentrated to give the Compound (I-b).

[1267] Next, a method for producing the Compound (I-c) from the Compound (I-b) is described.

[1268] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of them.

[1269] Examples of the oxidizing agent to be used in the reaction include mCPBA and hydrogen peroxide.

[1270] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be used as needed.

[1271] Examples of the base to be used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used at a ratio of 0.01 to 1 mol relative to 1 mol of the Compound (I-b).

[1272] Examples of the catalyst to be used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used at a ratio of 0.01 to 0.5 mol relative to 1 mol of the Compound (I-b).

[1273] In the reaction, the oxidizing agent is usually used at a ratio of 1 to 2 mol relative to 1 mol of the Compound (I-b).

[1274] The reaction temperature is usually within the range of −20 to 120° C. The reaction time is usually within the range of 0.1 to 12 hours(s).

[1275] When the reaction is completed, to the reaction mixture is added water, the resulting mixture is subjected to extraction with organic solvent(s), and the resulting organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen carbonate) as needed. The resulting organic layer is dried and / or concentrated to give the Compound (I-c).

[1276] Also, the Compound (I-c) may be prepared in one step reaction (one-pot) by reacting the Compound (I-a) with an oxidizing agent.

[1277] The reaction may be carried out according to the method for producing the Compound (I-c) from the Compound (I-b) by usually using the oxidizing agent at a ratio of 2 to 5 mol relative to 1 mol of the Compound (I-a).Production Method 2

[1278] A compound represented by formula (I-1-A) (hereinafter referred to as “Compound (I-1-A)”) may be prepared by reacting a compound represented by formula (M1-1-A) (hereinafter referred to as “Compound (M1-1-A)”) with a compound represented by formula (M2-1) (hereinafter referred to as “Compound (M2-1)”) in the presence of a condensing agent.

[1279] [wherein RA represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent (s) selected from Group U, a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent (s) selected from Group V; and the other symbols are the same as defined above.]

[1280] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as “THF”) and methyl tert-butyl ether (hereinafter referred to as “MTBE”) (hereinafter collectively referred to as “ethers”); halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter collectively referred to as “aromatic hydrocarbons”); esters such as ethyl acetate and butyl acetate (hereinafter collectively referred to as “esters”); nitriles; aprotic polar solvents such as N-methylpyrrolidone (hereinafter referred to as “NMP”), N,N-dimethylformamide (hereinafter referred to as “DMF”), and dimethyl sulfoxide (hereinafter referred to as “DMSO”) (hereinafter collectively referred to as “aprotic polar solvents”); nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine, and quinoline (hereinafter collectively referred to as “nitrogen-containing aromatic compounds”); and mixtures of two or more of them.

[1281] Examples of the condensing agent to be used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[1282] In the reaction, a catalyst may be used as needed. Examples of the catalyst to be used in the reaction include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, the catalyst is usually used at a ratio of 0.01 to 0.5 mol relative to 1 mol of the Compound (M1-1-A).

[1283] In the reaction, a base may be used as needed. Examples of the base to be used in the reaction include organic bases such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter collectively referred to as “organic bases”). When a base is used in the reaction, the base is usually used at a ratio of 1 to 2 mol relative to 1 mol of the Compound (M1-1-A).

[1284] In the reaction, the Compound (M2-1) is usually used at a ratio of 1 to 2 mol, and the condensing agent is usually used at a ratio of 1 to 2 mol, relative to 1 mol of the Compound (M1-1-A).

[1285] The reaction temperature is usually within the range of 0 to 200° C. The reaction time is usually within the range of 0.1 to 12 hours(s).

[1286] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-1-A).

[1287] The Compound (M2-1) is a commercially available compound or may be prepared by using known method(s).Production Method 3

[1288] The Compound (I-1-A) may also be prepared by reacting the Compound (M1-1-A) with a compound represented by formula (M2-2) (hereinafter referred to as “Compound (M2-2)”).

[1289] [wherein the symbols are the same as defined above.]

[1290] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers; aliphatic hydrocarbons such as hexane, heptane, and octane (hereinafter collectively referred to as “aliphatic hydrocarbons”); aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents; and mixtures of two or more of them.

[1291] In the reaction, a base may be used as needed. Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter collectively referred to as “alkali metal carbonates”); alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter collectively referred to as “alkali metal hydroxides”); and organic bases. When a base is used in the reaction, the base is usually used at a ratio of 1 to 2 mol relative to 1 mol of the Compound (M1-1-A).

[1292] In the reaction, the Compound (M2-2) is usually used at a ratio of 0.8 to 1.2 mol relative to 1 mol of the Compound (M1-1-A).

[1293] The reaction temperature is usually within the range of −20 to 200° C. The reaction time is usually within the range of 0.1 to 24 hours (s).

[1294] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent (s), and drying and / or concentrating the resulting organic layer to give the Compound (I-1-A).

[1295] The Compound (M2-2) is a commercially available compound or may be prepared by using known method(s).Production Method 4

[1296] A compound represented by formula (I-2-B) (hereinafter referred to as “Compound (I-2-B)”) may be prepared by reacting the compound represented by formula (II) (hereinafter referred to as “Compound (II)”) with a compound represented by formula (R-1) (hereinafter referred to as “Compound (R-1)”) in the presence of a base.

[1297] [wherein RB represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group U, C(O)R51, C(O)OR51, or C(O)NR51R52; L represents a leaving group such as a chlorine atom and a bromine atom; and the other symbols are the same as defined above.]

[1298] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1299] Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter collectively referred to as “alkali metal hydrides”), alkali metal carbonates, and organic bases.

[1300] In the reaction, the Compound (R-1) is usually used at a ratio of 1 to 5 mol, and the base is usually used at a ratio of 1 to 2 mol, relative to 1 mol of the Compound (II).

[1301] The reaction temperature is usually within the range of 0 to 100° C. The reaction time is usually within the range of 0.1 to 24 hours(s).

[1302] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-2-B).

[1303] The Compound (R-1) is a commercially available compound or may be prepared by using known method(s).Production Method 5

[1304] A compound represented by formula (I-1) (hereinafter referred to as “Compound (I-1)”) may be prepared by reacting a compound represented by formula (M1-2) (hereinafter referred to as “Compound (M1-2)”) with a compound represented by formula (M2-3) (hereinafter referred to as “Compound (M2-3)”).

[1305] [wherein V1 represents a halogen atom; and the other symbols are the same as defined above.]

[1306] When V1 represents a fluorine atom, the Compound (I-1 may be prepared by reacting the Compound (M1-2) with the Compound (M2-3) in the presence of a base.

[1307] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[1308] Examples of the base to be used in the reaction include alkali metal carbonates and alkali metal hydrides.

[1309] In the reaction, the Compound (M2-3) is usually used at a ratio of 0.8 to 1.2 mol, and the base is usually used at a ratio of 1 to 2 mol, relative to 1 mol of the Compound (M1-2).

[1310] The reaction temperature is usually within the range of 0 to 200° C. The reaction time is usually within the range of 0.5 to 24 hours(s).

[1311] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-1).

[1312] When V1 represents a chlorine atom, a bromine atom, or an iodine atom, the Compound (I-1) may be prepared by reacting the Compound (M1-2) with the Compound (M2-3) in the presence of a base and a copper catalyst or a palladium catalyst.

[1313] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[1314] Examples of the base to be used in the reaction include alkali metal carbonates; phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydrides; organic bases; and cyclic amines such as 1,4-diazabicyclo[2,2,2]octane and diazabicycloundecene.

[1315] Examples of the copper catalyst to be used in the reaction include copper(I) iodide, copper(I) bromide, copper(I) chloride, and copper(I) oxide. When a copper catalyst is used in the reaction, the copper catalyst is usually used at a ratio of 0.01 to 0.5 mol relative to 1 mol of the Compound (M1-2).

[1316] Examples of the palladium catalyst to be used in the reaction include palladium(II) acetate and tris(dibenzylideneacetone)dipalladium(0). When a palladium catalyst is used in the reaction, the palladium catalyst is usually used at a ratio of 0.01 to 0.2 mol relative to 1 mol of the Compound (M1-2).

[1317] In the reaction, a ligand may be used as needed. Examples of the ligand to be used in the reaction include acetylacetone, salen, phenanthroline, triphenylphosphine, and 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene. When a ligand is used in the reaction, the ligand is usually used at a ratio of 0.01 to 0.5 mol relative to 1 mol of the Compound (M1-2).

[1318] In the reaction, the Compound (M2-3) is usually used at a ratio of 0.8 to 1.2 mol, and the base is usually used at a ratio of 1 to 2 mol, relative to 1 mol of the Compound (M1-2).

[1319] The reaction temperature is usually within the range of 0 to 200° C. The reaction time is usually within the range of 0.5 to 24 hours(s).

[1320] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-1).

[1321] A compound according to the Compound (M2-3) wherein R1 represents RA or RB is a commercially available compound or may be prepared by using known method(s).Production Method 6

[1322] The Compound (I-a) may be prepared according to the following scheme.

[1323] [wherein Xa represents a chlorine atom, a bromine atom, or an iodine atom; Xb represents SR2 or a hydrogen atom; and the other symbols are the same as defined above.]

[1324] First, a step to produce a compound represented by formula (M3-1) (hereinafter referred to as “Compound (M3-1)”) from a compound represented by formula (III-1) (hereinafter referred to as “Compound (III-1)”) (hereinafter referred to as “Step 6-A”) is described.

[1325] The Compound (M3-1) may be prepared by reacting the Compound (III-1) with a halogenating agent.

[1326] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of them.

[1327] Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide.

[1328] In the reaction, the halogenating agent is usually used at a ratio of 1 to 20 mol relative to 1 mol of the Compound (III-1).

[1329] The reaction temperature is usually within the range of −20 to 200° C. The reaction time is usually within the range of 0.1 to 72 hours(s).

[1330] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (M3-1).

[1331] Next, a step to produce the Compound (I-a) from the Compound (M3-1) is described.

[1332] The Compound (I-a) may be prepared by reacting the Compound (M3-1) with a compound represented by formula (R-2) (hereinafter referred to as “Compound (R-2)”) in the presence of a metal catalyst and a base.

[1333] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[1334] Examples of the metal catalyst to be used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride.

[1335] Examples of the base to be used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[1336] In the reaction, a ligand may be used. Examples of the ligand include triphenylphosphine, Xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is usually used at a ratio of 0.01 to 1 mol relative to 1 mol of the Compound (M3-1).

[1337] In the reaction, the Compound (R-2) is usually used at a ratio of 1 to 20 mol, the metal catalyst is usually used at a ratio of 0.01 to 0.5 mol, and the base is usually used at a ratio of 0.1 to 5 mol, relative to 1 mol of the Compound (M3-1).

[1338] The reaction temperature is usually within the range of −20 to 200° C. The reaction time is usually within the range of 0.1 to 72 hours(s).

[1339] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-a).

[1340] The Compound (R-2) is known or may be prepared according to known method(s).

[1341] Next, a step to produce the Compound (I-a) from the Compound (III-1) is described.

[1342] The Compound (I-a) may also be prepared by reacting the Compound (III-1) with a compound represented by formula (R-3) (hereinafter referred to as “Compound (R-3)”) in the presence of a halogenating agent.

[1343] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[1344] Examples of the halogenating agent include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, and potassium iodide.

[1345] In the reaction, an oxidizing agent may be used as needed. Examples of the oxidizing agent to be used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, and DMSO. When an oxidizing agent is used in the reaction, the oxidizing agent is usually used at a ratio of 1 to 20 mol relative to 1 mol of the Compound (III-1).

[1346] In the reaction, the Compound (R-3) is usually used at a ratio of 0.5 to 10 mol, and the halogenating agent is usually used at a ratio of 0.05 to 10 mol, relative to 1 mol of the Compound (III-1).

[1347] The reaction temperature is usually within the range of 0 to 200° C. The reaction time is usually within the range of 0.1 to 72 hours(s).

[1348] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-a).

[1349] The Compound (R-3) is known or may be prepared according to known method(s).Production Method 7

[1350] A compound represented by formula (I-S) (hereinafter referred to as “Compound (I-S)”) may be prepared by reacting the Compound (I-1) with a sulfating agent.

[1351] [wherein the symbols are the same as defined above.]

[1352] The reaction is carried out in a solvent or in the absence of a solvent. Examples of the solvent include ethers, halogenated hydrocarbons, aromatic hydrocarbons, nitriles, nitrogen-containing aromatic compounds, and mixtures of two or more of them.

[1353] Examples of the sulfating agent include phosphorus pentasulfide and Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide).

[1354] In the reaction, the sulfating agent is usually used at a ratio of 1 to 3 mol relative to 1 mol of the Compound (I-1).

[1355] The reaction temperature is usually within the range of 0 to 200° C. The reaction time is usually within the range of 1 to 24 hours(s).

[1356] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent (s), and drying and / or concentrating the resulting organic layer to give the Compound (I-S).Production Method 8

[1357] A compound represented by formula (II-S) (hereinafter referred to as “Compound (II-S)”) may be prepared by reacting the Compound (II-O) with a sulfating agent.

[1358] [wherein the symbols are the same as defined above.]

[1359] The reaction may be carried out according to the Production method 7 by using the Compound (II-O) instead of the Compound (I-1).Production Method 9

[1360] A compound represented by formula (I-3-H) (hereinafter referred to as “Compound (I-3-H)”) may be prepared by reacting a compound represented by formula (M4-1) (hereinafter referred to as “Compound (M4-1)”) with a reducing agent.

[1361] [wherein the symbols are the same as defined above.]

[1362] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, alcohols, and mixtures of two or more of them.

[1363] Examples of the reducing agent to be used in the reaction include sodium borohydride, sodium cyanoborohydride, and lithium aluminum hydride.

[1364] In the reaction, the reducing agent is usually used at a ratio of 1 to 2 mol relative to 1 mol of the Compound (M4-1).

[1365] The reaction temperature is usually within the range of 0 to 100° C. The reaction time is usually within the range of 0.1 to 24 hours(s).

[1366] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (I-3-H).Production Method 10

[1367] A compound represented by formula (I-3-C) may be prepared by reacting the Compound (I-3-H) with a compound represented by formula (R-4) (hereinafter referred to as “Compound (R-4)”) in the presence of a base.

[1368] [wherein Rc represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent (s) selected from Group X, a C3-C7 cycloalkyl group optionally substituted with one or more substituent (s) selected from Group Y, C(O)R46, C(O)OR46, or C(O)NR46R47; and the other symbols are the same as defined above.]

[1369] The reaction may be carried out according to the Production method 4 by using the Compound (I-3-H) instead of the Compound (II).

[1370] The Compound (R-4) is a commercially available compound or may be prepared by using known method(s).Production Method 11

[1371] An N-oxide of the compound represented by formula (I) may be prepared by reacting the compound represented by formula (I) with an oxidizing agent. The reaction may be carried out according to the method described in, for example, the Production method 1, US Patent Application Publication No. 2018 / 0009778, or WO 2016 / 121970 pamphlet.

[1372] Hereinafter, production methods for the production intermediate compounds are described.Reference Production Method 1

[1373] A compound represented by formula (M1-1-D) (hereinafter referred to as “Compound (M1-1-D)”) may be prepared by reacting a compound represented by formula (M1-3) (hereinafter referred to as “Compound (M1-3)”) with a compound represented by formula (R-5) (hereinafter referred to as “Compound (R-5)”) in the presence of a base.

[1374] [wherein RD represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W, or a C3-C7 cycloalkyl group optionally substituted with one or more substituent (s) selected from Group U; and the other symbols are the same as defined above.]

[1375] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1376] Examples of the base to be used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[1377] In the reaction, the Compound (R-5) is usually used at a ratio of 1 to 5 mol, and the base is usually used at a ratio of 1 to 2 mol, relative to 1 mol of the Compound (M1-3).

[1378] The reaction temperature is usually within the range of 0 to 100° C. The reaction time is usually within the range of 0.1 to 24 hours(s).

[1379] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (M1-1-D).Reference Production Method 2

[1380] The Compound (M1-1-A) may be prepared by reacting a compound represented by formula (M1-2-2) (hereinafter referred to as “Compound (M1-2-2)”) with a compound represented by formula (R-6) (hereinafter referred to as “Compound (R-6)”)

[1381] [wherein Xd represents a fluorine atom or a chlorine atom; and the other symbols are the same as defined above.]

[1382] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include aprotic polar solvents, alcohols, and mixtures of two or more of them.

[1383] In the reaction, a base may be used as needed. Examples of the base to be used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used at a ratio of 0.1 to 5 mol relative to 1 mol of the Compound (M1-2-2).

[1384] In the reaction, the Compound (R-6) is usually used at a ratio of 1 to 100 mol relative to 1 mol of the Compound (M11-2-2).

[1385] The reaction temperature is usually within the range of 25 to 200° C. The reaction time is usually within the range of 01 to 48 hours(s).

[1386] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent (s), and drying and / or concentrating the resulting organic layer to give the Compound (M1-1-A).

[1387] The Compound (R-6) is a commercially available compound or may be prepared by using known method(s).Reference Production Method 3

[1388] The Compound (M1-3) may be prepared by reacting the Compound (M1-2-2) with ammonia.

[1389] [wherein the symbols are the same as defined above,]

[1390] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, nitriles, aprotic polar solvents, alcohols, water, and mixtures of two or more of them.

[1391] In the reaction, a base may be used as needed, Examples of the base to be used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used at a ratio of 0.1 to 5 mol relative to 1 mol of the Compound (M1-2-2).

[1392] The ammonia may also be used as a solution such as an ammonia solution in water and an ammonia solution in methanol.

[1393] In the reaction, the ammonia is usually used at a ratio of 1 to 100 mol relative to 1 mol of the Compound (M1-2-2).

[1394] The reaction temperature is usually within the range of −20 to 100° C. The reaction time is usually within the range of 0.1 to 48 hours(s).

[1395] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (M1-3).Reference Production Method 4

[1396] A compound represented by formula (M1-2b) and a compound represented by formula (M1-2c) may be prepared by reacting a compound represented by formula (M1-2a) (hereinafter referred to as “Compound (M1-2a)”) with an oxidizing agent. The compound represented by formula (M1-2c) may also be prepared by reacting the compound represented by formula (M1-2b) with an oxidizing agent.

[1397] [wherein the symbols are the same as defined above.]

[1398] These reactions may be carried out according to the Production method 1.Reference Production Method 5

[1399] The Compound (M1-2a) may be prepared according to the following scheme.

[1400] [wherein the symbols are the same as defined above.]

[1401] These reactions may be carried out according to the Production method 6.

[1402] A compound represented by formula (M1-4) (hereinafter referred to as “Compound (M1-4)”) is known or may be prepared according to the method(s) described in, for example, WO 2015 / 157093 pamphlet, WO 2016 / 109706 pamphlet, Organic & Biomolecular Chemistry, 2017, 15, 4199, or European Journal of Medicinal Chemistry, 2016, 123, 916.Reference Production Method 6

[1403] The Compound (II-˜) may be prepared by reacting the Compound (M1-3) with the Compound (M2-1) or the Compound (M2-2).

[1404] [wherein the symbols are the same as defined above.]

[1405] These reactions may be carried out according to the Production method 2 or the Production method 3 by using the Compound (M1-3) instead of the Compound (M1-1-A).Reference Production Method 7

[1406] A compound represented by formula (M3-1-A) may be prepared by reacting a compound represented by formula (M1-6-A) (hereinafter referred to as “Compound (M1-6-A)”) with the Compound (M2-1) or the Compound (M2-2),

[1407] [wherein the symbols are the same as defined above.]

[1408] These reactions may be carried out according to the Production method 2 or the Production method 3 by using the Compound (M1-6-A) instead of the Compound (M1-1-A).Reference Production Method 8

[1409] A compound represented by formula (M1-6-D) (hereinafter referred to as “Compound (M1˜6-D)”) may be prepared according to the following scheme.

[1410] [wherein the symbols are the same as defined above.]

[1411] First, a method for producing a compound represented by formula (M1-7) (hereinafter referred to as “Compound (M1-7)”) is described.

[1412] The Compound (M1-7) may be prepared by reacting a compound represented by formula (M1-5) (hereinafter referred to as “Compound (M1-5)”) with ammonia. The reaction may be carried out according to the Reference Production method 3 by using the Compound (M1-5) instead of the Compound (M1-2-2).

[1413] Next, a method for producing the Compound (M1-6-D) is described.

[1414] The Compound (M1-6-D) may be prepared by reacting the Compound (M1-7) with the Compound (R-5) in the presence of a base. The reaction may be carried out according to the Reference Production method 1 by using the Compound (M1-7) instead of the Compound (M1-3).Reference Production Method 9

[1415] The Compound (M1-6-A) may be prepared according to the following scheme.

[1416] [wherein the symbols are the same as defined above.]

[1417] First, a method for producing a compound represented by formula (M1-8-A) (hereinafter referred to as “Compound (M1-8-A)”) is described.

[1418] The Compound (M1-8-A) may be prepared by reacting the Compound (M1-4) with the Compound (R-6). The reaction may be carried out according to the Reference Production method 2 by using the Compound (M1-4) instead of the Compound (M1-2-2).

[1419] Next, a method for producing the Compound (M1-6-A) is described.

[1420] The Compound (M1-6-A) may be prepared by reacting the Compound (M1-8-A) with a halogenating agent. The reaction may be carried out according to the Step 6-A in the Production method 6 by using the Compound (M1-8-A) instead of the Compound (III-1).Reference Production Method 10

[1421] A compound represented by formula (M3-1-B) (hereinafter referred to as “Compound (M3-1-B)”) may be prepared according to the following scheme.

[1422] [wherein the symbols are the same as defined above.]

[1423] First, a method for producing a compound represented by formula (M3-2) (hereinafter referred to as “Compound (M3-2)”) is described.

[1424] The Compound (M3-2) may be prepared by reacting the Compound (M1-7) with the Compound (M2-1) or the Compound (M2-2). These reactions may be carried out according to the Production method 2 or the Production method 3 by using the Compound (M1-7) instead of the Compound (M1-1-A).

[1425] Next, a method for producing the Compound (M3-1-B) is described.

[1426] The Compound (M3-1-B) may be prepared by reacting the Compound (M3-2) with the Compound (R-1) in the presence of a base. The reaction may be carried out according to the Production method 4 by using the Compound (M3-2) instead of the Compound (II)Reference Production Method 11

[1427] A compound represented by formula (III-1-A) (hereinafter referred to as “Compound (III-1-A)”) may be prepared according to the following scheme,

[1428] [wherein the symbols are the same as defined above,]

[1429] The Compound (III-1-A) may be prepared by reacting the Compound (M1-8-A) with the Compound (M2-1) or the Compound (M2-2). These reactions may be carried out according to the Production method 2 or the Production method 3 by using the Compound (M1-M-A) instead of the CompoundReference Production Method 12

[1430] A compound represented by formula (III-1-B) (hereinafter referred to as “Compound (III-1-B)”) may be prepared according to the following scheme,

[1431] [wherein the symbols are the same as defined above.]

[1432] First, a method for producing a compound represented by formula (III-2-B) (hereinafter referred to as “Compound (III-2-B)”) is described.

[1433] The Compound (III-2-B) may be prepared by reacting a compound represented by formula (M1-9) (hereinafter referred to as “Compound (M1-9)”) with the Compound (M2-1) or the Compound (M2-2). These reactions may be carried out according to the Production method 2 or the Production method 3 by using the Compound (M1-9) instead of the Compound (M1-1-A).

[1434] Next, a method for producing the Compound (III-1-B) is described.

[1435] The Compound (III-1-B) may be prepared by reacting the Compound (III-2-B) with the Compound (R-1) in the presence of a base. The reaction may be carried out according to the Production method 4 by using the Compound (III-2-B) instead of the Compound (II).Reference Production Method 13

[1436] The Compound (M1-9) may be prepared by reacting the Compound (M1-4) with ammonia.

[1437] [wherein the symbols are the same as defined above.]

[1438] The reaction may be carried out according to the Reference Production method 3 by using the Compound (M1-4) instead of the Compound (M1-2-2.Reference Production Method 14

[1439] A compound represented by formula (III-1-P) (hereinafter referred to as “Compound (III-1-P)”) may be prepared by reacting a compound represented by formula (M2-3-P) (hereinafter referred to as “Compound (M2-3-P)) with the Compound (M1-4).

[1440] [wherein the symbols are the same as defined above.]

[1441] The reaction may be carried out according to the Production method 5 by using the Compound (M1-4) instead of the Compound (M1-2), and using the Compound (M2-3-P) instead of the Compound (M2-3),Reference Production Method 15

[1442] The Compound (M4-1) may be prepared according to the following scheme.

[1443] [wherein R60 represents a methyl group or an ethyl group; and the other symbols are the same as defined above.]

[1444] First, a method for producing a compound represented by formula (M5) (hereinafter referred to as “Compound (M5)”) is described.

[1445] The Compound (M5) may be prepared by reacting a compound represented by formula (M6) (hereinafter referred to as “Compound (M6)”) with the Compound (M1-3).

[1446] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1447] In the reaction, a base may be used as needed. Examples of the base include organic bases. When a base is used in the reaction, the base is usually used at a ratio of 1 to 5 mol relative to 1 mol of the Compound (M6).

[1448] In the reaction, the Compound (M1-3) is usually used at a ratio of 1 to 5 mol relative to 1 mol of the Compound (M6).

[1449] The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.5 to 12 hours(s).

[1450] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, then subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (M5).

[1451] The Compound (M6) may be prepared according to the method(s) described in, for example, Journal of Biological Chemistry, 2016, 291, 14146.

[1452] Next, a method for producing the Compound (M4-1) from the Compound (M5) is described.

[1453] The Compound (M4-1) may be prepared by reacting the Compound (M5) with a compound represented by formula (R-7) (hereinafter referred to as “Compound (R-7)”).

[1454] The reaction is usually carried out in a solvent or in the absence of a solvent. Examples of the solvent include ethers, aromatic hydrocarbons, halogenated hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1455] In the reaction, the Compound (R-7) is usually used at a ratio of 1 to 50 mol relative to 1 mol of the Compound (M5).

[1456] In the reaction, an acid or a base may be used as needed.

[1457] Examples of the acid to be used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid. When an acid is used in the reaction, the acid is usually used at a ratio of 0.01 to 5 mol relative to 1 mol of the Compound (M5).

[1458] Examples of the base to be used in the reaction include organic bases. When a base is used in the reaction, the base is usually used at a ratio of 1 to 5 mol relative to 1 mol of the Compound (M5).

[1459] The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.5 to 24 hours(s).

[1460] When the reaction is completed, the reaction mixture may be subjected to a work-up such as adding water to the reaction mixture, subjecting the resulting mixture to extraction with organic solvent(s), and drying and / or concentrating the resulting organic layer to give the Compound (M4-1).

[1461] The Compound (R-7) is a commercially available compound or may be prepared by using known method(s).

[1462] Also, the Compound (M4-1) may be prepared in one step reaction (one-pot) by reacting the Compound (M6), the Compound (M1-3), and the Compound (R-7).

[1463] The reaction may be carried out according to the method for producing the Compound (M4-1) from the Compound (M5) by usually using the Compound (M1-3) at a ratio of 1 to 5 mol, and usually using the Compound (R-7) at a ratio of 1 to 50 mol, relative to 1 mol of the Compound (M6).Reference Production Method 16

[1464] The Compound (M2-3-P) may be prepared by reacting a compound represented by formula (M7) (hereinafter referred to as “Compound (M7)”) with a compound represented by formula (R-8) (hereinafter referred to as “Compound (R-8)”).

[1465] [wherein the symbols are the same as defined above.]

[1466] The reaction may be carried out according to the method(s) described in, for example, Organic Letters, 2020, 22, 3825.

[1467] The Compound (M7) and the Compound (R-8) are commercially available compounds or may be prepared by using known methods.

[1468] The Present compound or the Present compound X may be mixed with or used in combination with one or more ingredient (s) selected from the group consisting of the following Group (a), Group (b), Group (c), and Group (d) (hereinafter referred to as “Present ingredient”).

[1469] When the Present compound or the Present compound X is mixed with or used in combination with the Present ingredient, they are used simultaneously, separately, or at time intervals with each other.

[1470] When the Present compound or the Present compound X is used simultaneously with the Present ingredient, the Present compound or the Present compound X and the Present ingredient may be contained in separate formulations or contained in one formulation.

[1471] One aspect of the present invention provides a composition comprising one or more ingredient (s) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the Present compound.

[1472] One aspect of the present invention provides a composition comprising one or more ingredient (s) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the Present compound X (hereinafter referred to as “Composition A”).

[1473] Group (a) is a group consisting of acetylcholinesterase inhibitors (for example, carbamate insecticides and organophosphate insecticides), GABA-gated chloride channel blockers (for example, phenylpyrazole insecticides), sodium channel modulators (for example, pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (for example, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (for example, macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial disruptors of insect midgut membranes, inhibitors of mitochondrial ATP synthase, uncouplers of oxidative phosphorylation, nicotinic acetylcholine receptor channel blockers (for example, nereistoxin insecticides), inhibitors of chitin biosynthesis, moulting disruptors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial complexes I, II, III, and IV electron transport inhibitors, voltage-dependent sodium channel blockers, inhibitors of acetyl CoA carboxylase, ryanodine receptor modulators (for example, diamide insecticides), chordotonal organ modulators, and microbial insecticides, and other insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients. These ingredients are described in the classification on the basis of action mechanism by IRAC.

[1474] Group (b) is a group consisting of nucleic acids synthesis inhibitors (for example, phenylamide fungicides and acylamino acid fungicides), cell division and cytoskeleton inhibitors (for example, MBC fungicides), respiration inhibitors (for example, QoI fungicides and QiI fungicides), amino acids synthesis and protein synthesis inhibitors (for example, anilino-pyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (for example, DMI fungicides such as triazole fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, fungicides with multi-site contact activity, microbial fungicides, and other fungicidal active ingredients. These ingredients are described in the classification on the basis of action mechanism by FRAC.

[1475] Group (c) is a group of plant growth regulatory ingredients (including mycorrhizal fungi and root nodule bacteria).

[1476] Group (d) is a group of repellent ingredients.

[1477] Hereinafter, examples of the combination of the Present ingredient and the Present compound X are described. For example, “alanycarb+SX” indicates a combination of alanycarb and SX.

[1478] The abbreviation of “SX” indicates any one of the Present compound X selected from the Compound groups SX1 to SX2299 described in Examples. Also, all of the following Present ingredient are known ingredients, and may be obtained from commercially available formulations, or may be prepared by known methods. When the Present ingredient is a microorganism, it may also be available from a bacterial authority depository. Further, the number in parentheses represents the CAS RN (registered trademark).

[1479] Combinations of the Present ingredient in the above Group (a) and the Present compound X:

[1480] abamectin+SX, acephate+SX, acequinocyl+SX, acetamiprid+SX, acetoprole+SX, acrinathrin+SX, acynonapyr+SX, afidopyropen+SX, afoxolaner+SX, alanycarb+SX, aldicarb+SX, allethrin+SX, alpha-cypermethrin+SX, alpha-endosulfan+SX, aluminium phosphide+SX, amitraz+SX, azadirachtin+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX, azocyclotin+SX, bark of Celastrus angulatus+SX, bendiocarb+SX, benfluthrin+SX, benfuracarb+SX, bensultap+SX, benzoximate+SX, benzpyrimoxan+SX, beta-cyfluthrin+SX, beta-cypermethrin+SX, bifenazate+SX, bifenthrin+SX, bioallethrin+SX, bioresmethrin+SX, bistrifluron+SX, borax+SX, boric acid+SX, broflanilide+SX, bromopropylate+SX, buprofezin+SX, butocarboxim+SX, butoxycarboxim+SX, cadusafos+SX, calcium phosphide+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride+SX, cartap+SX, chinomethionat+SX, chlorantraniliprole+SX, chlordane+SX, chlorethoxyfos+SX, chlorfenapyr+SX, chlorfenvinphos+SX, chlorfluazuron+SX, chlormephos+SX, chloropicrin+SX, chlorpyrifos+SX, chlorpyrifos-methyl+SX, chromafenozide+SX, clofentezine+SX, clothianidin+SX, concanamycin A+SX, coumaphos+SX, cryolite+SX, cyanophos+SX, cyantraniliprole+SX, cyclaniliprole+SX, cyclobutrifluram+SX, cycloprothrin+SX, cycloxaprid+SX, cyenopyrafen+SX, cyetpyrafen+SX, cyflumetofen+SX, cyfluthrin+SX, cyhalodiamide+SX, cyhalothrin+SX, cyhexatin+SX, cypermethrin+SX, cyphenothrin+SX, cyproflanilide+SX, cyromazine+SX, dazomet+SX, deltamethrin+SX, demeton-S-methyl+SX, diafenthiuron+SX, diazinon+SX, dichlorvos+SX, dicloromezotiaz+SX, dicofol+SX, dicrotophos+SX, diflovidazin+SX, diflubenzuron+SX, dimefluthrin+SX, dimethoate+SX, dimethylvinphos+SX, dimpropyridaz+SX, dinotefuran+SX, disodium octaborate+SX, disulfoton+SX, DNOC(2-methyl-4,6-dinitrophenol)+SX, doramectin+SX, dried leaves of Dryopteris filix-mas+SX, emamectin-benzoate+SX, empenthrin+SX, endosulfan+SX, EPN(O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, epsilon-metofluthrin+SX, epsilon-momfluorothrin+SX, esfenvalerate+SX, ethiofencarb+SX, ethion+SX, ethiprole+SX, ethoprophos+SX, etofenprox+SX, etoxazole+SX, extract of Artemisia absinthium+SX, extract of Azadirachta indica+SX, extract of Cassia nigricans+SX, extract of clitoria ternatea+SX, extract of Symphytum officinale+SX, extract or simulated blend of Chenopodium ambrosioides+SX, extract of Tanacetum vulgare+SX, extract of Urtica dioica+SX, extract of Viscum album+SX, famphur+SX, fenamiphos+SX, fenazaquin+SX, fenbutatin oxide+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, flometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX, fluchlordiniliprole+SX, flucycloxuron+SX, flucythrinate+SX, fluensulfone+SX, flufenoprox+SX, flufenoxuron+SX, flufiprole+SX, flumethrin+SX, flupentiofenox+SX, flupyradifurone+SX, flupyrimin+SX, fluralaner+SX, fluvalinate+SX, fluxametamide+SX, formetanate+SX, fosthiazate+SX, furamethrin+SX, furathiocarb+SX, gamma-cyhalothrin+SX, GS-omega / kappa HXTX-Hvla peptide+SX, halfenprox+SX, halofenozide+SX, heptafluthrin+SX, heptenophos+SX, hexaflumuron+SX, hexythiazox+SX, potassium salt of hop beta acid+SX, hydramethylnon+SX, hydroprene+SX, imicyafos+SX, imidacloprid+SX, imidaclothiz+SX, imiprothrin+SX, indazapyroxamet+SX, indoxacarb+SX, isocycloseram+SX, isofenphos+SX, isoprocarb+SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate+SX, isoxathion+SX, ivermectin+SX, kadethrin+SX, kappa-tefluthrin+SX, kappa-bifenthrin+SX, kinoprene+SX, lambda-cyhalothrin+SX, lenoremycin+SX, lepimectin+SX, lime sulfur+SX, lotilaner+SX, lufenuron+SX, machine oil+SX, malathion+SX, mecarbam+SX, meperfluthrin+SX, metaflumizone+SX, metam+SX, methamidophos+SX, methidathion+SX, methiocarb+SX, methomyl+SX, methoprene+SX, methoxychlor+SX, methoxyfenozide+SX, methyl bromide+SX, metofluthrin+SX, metolcarb+SX, metoxadiazone+SX, mevinphos+SX, milbemectin+SX, milbemycin oxime+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX, nicofluprole+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX, novaluron+SX, noviflumuron+SX, oil of the seeds of Chenopodium anthelminticum+SX, omethoate+SX, oxamyl+SX, oxazosulfyl+SX, oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, permethrin+SX, phenothrin+SX, phenthoate+SX, phorate+SX, phosalone+SX, phosmet+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginate+SX, prothiofos+SX, pyflubumide+SX, pymetrozine+SX, pyraclofos+SX, pyrethrins+SX, pyridaben+SX, pyridalyl+SX, pyridaphenthion+SX, pyrifluquinazone+SX, pyrimidifen+SX, pyriminostrobin+SX, pyriprole+SX, pyriproxyfen+SX, quinalphos+SX, resmethrin+SX, rotenone+SX, ryanodine+SX, sarolaner+SX, selamectin+SX, sigma-cypermethrin+SX, silafluofen+SX, sodium borate+SX, sodium metaborate+SX, spidoxamat+SX, spinetoram+SX, spinosad+SX, spirodiclofen+SX, spiromesifen+SX, spiropidion+SX, spirotetramat+SX, sulfluramid+SX, sulfotep+SX, sulfoxaflor+SX, sulfur+SX, sulfuryl fluoride+SX, tartar emetic+SX, tau-fluvalinate+SX, tebufenozide+SX, tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX, temephos+SX, terbufos+SX, terpene constituents of the extract of chenopodium ambrosioides near ambrosioides+SX, tetrachlorantraniliprole+SX, tetrachlorvinphos+SX, tetradifon+SX, tetramethrin+SX, tetramethylfluthrin+SX, tetraniliprole+SX, theta-cypermethrin+SX, thiacloprid+SX, thiamethoxam+SX, thiocyclam+SX, thiodicarb+SX, thiofanox+SX, thiometon+SX, thiosultap-disodium+SX, thiosultap-monosodium+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, vamidothion+SX, wood extract of Quassia amara+SX, XMC (3,5-dimethylphenyl N-methylcarbamate)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphide+SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3)+SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5)+SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5)+SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6)+SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9)+SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2)+SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3)+SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0)+SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide+SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b] [1,4]oxazepin-10-one (2607927-97-7)+SX, BT crop protein Cry1Ab+SX, BT crop protein Cry1Ac+SX, BT crop protein Cry1Fa+SX, BT crop protein Cry1A.105+SX, BT crop protein Cry2Ab+SX, BT crop protein Vip3A+SX, BT crop protein mCry3A+SX, BT crop protein Cry3Ab+SX, BT crop protein Cry3Bb+SX, BT crop protein Cry34Ab1 / Cry35Ab1+SX, Adoxophyes orana granulosis virus strain BV-0001+SX, Anticarsia gemmatalis mNPV+SX, Autographa californica mNPV+SX, Cydia pomonella GV strain V15+SX, Cydia pomonella GV strain V22+SX, Cryptophlebia leucotreta GV+SX, Dendrolimus punctatus cypovirus+SX, Helicoverpa armigera NPV strain BV-0003+SX, Helicoverpa zea NPV+SX, Lymantria dispar NPV+SX, Mamestra brassicae NPV+SX, Mamestra configurata NPV+SX, Neodiprion abietis NPV+SX, Neodiprion lecontei NPV+SX, Neodiprion sertifer NPV+SX, Nosema locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodoptera exigua mNPV+SX, Spodoptera littoralis mNPV+SX, Spodoptera litura NPV+SX, Arthrobotrys dactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637+SX, Bacillus megaterium+SX, Bacillus sp. strain AQ175+SX, Bacillus sp. strain AQ177+SX, Bacillus sp. strain AQ178+SX, Bacillus sphaericus strain 2362 serotype H5a5b+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus sphaericus Serotype strain H5a5b+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD #32+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7+SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306)+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348+SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki strain F810+SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002+SX, Bacillus thuringiensis subsp. morrisoni+SX, Bacillus thuringiensis var. colmeri+SX, Bacillus thuringiensis var. darmstadiensis strain 24-91+SX, Bacillus thuringiensis var. dendrolimus+SX, Bacillus thuringiensis var. galleriae+SX, Bacillus thuringiensis var. israelensis strain BMP144+SX, Bacillus thuringiensis var. israelensis serotype strain H-14+SX, Bacillus thuringiensis var. japonensis strain buibui+SX, Bacillus thuringiensis var. san diego strain M-7+SX, Bacillus thuringiensis var. 7216+SX, Bacillus thuringiensis var. aegypti+SX, Bacillus thuringiensis var. T36+SX, Beauveria bassiana strain ANT-03+SX, Beauveria bassiana strain ATCC74040+SX, Beauveria bassiana strain GHA+SX, Beauveria brongniartii+SX, Burkholderia rinojensis strain A396+SX, Chromobacterium subtsugae strain PRAA4-1T+SX, Dactyllela ellipsospora+SX, Dectylaria thaumasia+SX, Hirsutella minnesotensis+SX, Hirsutella rhossiliensis+SX, Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium lecanii strain KV01+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX, Lecanicillium lecanii conidia of strain DAOM216596+SX, Lecanicillium muscarium strain Ve6+SX, Metarhizium anisopliae strain F52+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52+SX, Metarhizium flavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomyces fumosoroseus Apopka strain 97+SX, Paecilomyces lilacinus strain 251+SX, Paecilomyces tenuipes strain T1+SX, Paenibacillus popilliae+SX, Pasteuria nishizawae strain Pn1+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecani strain NCIM1312+SX, Wolbachia pipientis+SX.

[1481] Combination of the Present ingredient in the above Group (b) and the Present compound X:

[1482] acibenzolar-S-methyl+SX, aldimorph+SX, ametoctradin+SX, aminopyrifen+SX, amisulbrom+SX, anilazine+SX, azaconazole+SX, azoxystrobin+SX, basic copper sulfate+SX, benalaxyl+SX, benalaxyl-M+SX, benodanil+SX, benomyl+SX, benthiavalicarb+SX, benthiavalicarb-isopropyl+SX, benzovindiflupyr+SX, binapacryl+SX, biphenyl+SX, bitertanol+SX, bixafen+SX, blasticidin-S+SX, Bordeaux mixture+SX, boscalid+SX, bromothalonil+SX, bromuconazole+SX, bupirimate+SX, captafol+SX, captan+SX, carbendazim+SX, carboxin+SX, carpropamid+SX, chinomethionat+SX, chitin+SX, chloroinconazide+SX, chloroneb+SX, chlorothalonil+SX, chlozolinate+SX, colletochlorin B+SX, copper(II) acetate+SX, copper(II) hydroxide+SX, copper oxychloride+SX, copper(II) sulfate+SX, coumoxystrobin+SX, cyazofamid+SX, cyflufenamid+SX, cymoxanil+SX, cyproconazole+SX, cyprodinil+SX, dichlobentiazox+SX, dichlofluanid+SX, diclocymet+SX, diclomezine+SX, dicloran+SX, diethofencarb+SX, difenoconazole+SX, diflumetorim+SX, dimethachlone+SX, dimethirimol+SX, dimethomorph+SX, dimoxystrobin+SX, diniconazole+SX, diniconazole-M+SX, dinocap+SX, dipotassium hydrogenphosphite+SX, dipymetitrone+SX, dithianon+SX, dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX, epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX, etridiazole+SX, extract of Melaleuca alternifolia+SX, extract of Reynoutria sachalinensis+SX, extract of the cotyledons of lupine plantlets (“BLAD”)+SX, extract of Allium sativum+SX, extract of Equisetum arvense+SX, extract of Tropaeolum majus+SX, famoxadone+SX, fenamidone+SX, fenaminstrobin+SX, fenarimol+SX, fenbuconazole+SX, fenfuram+SX, fenhexamid+SX, fenoxanil+SX, fenpiclonil+SX, fenpicoxamid+SX, fenpropidin+SX, fenpropimorph+SX, fenpyrazamine+SX, fentin acetate+SX, fentin chloride+SX, fentin hydroxide+SX, ferbam+SX, ferimzone+SX, florylpicoxamid+SX, fluazinam+SX, flubeneteram+SX, fludioxonil+SX, flufenoxadiazam+SX, flufenoxystrobin+SX, fluindapyr+SX, flumetylsulforim+SX, flumorph+SX, fluopicolide+SX, fluopyram+SX, fluopimomide+SX, fluoroimide+SX, fluoxapiprolin+SX, fluoxastrobin+SX, fluoxytioconazole+SX, fluquinconazole+SX, flusilazole+SX, flusulfamide+SX, flutianil+SX, flutolanil+SX, flutriafol+SX, fluxapyroxad+SX, folpet+SX, fosetyl+SX, fosetyl-aluminium+SX, fuberidazole+SX, furalaxyl+SX, furametpyr+SX, guazatine+SX, hexaconazole+SX, hymexazole+SX, imazalil+SX, imibenconazole+SX, iminoctadine+SX, iminoctadine triacetate+SX, inpyrfluxam+SX, iodocarb+SX, ipconazole+SX, ipfentrifluconazole+SX, ipflufenoquin+SX, iprobenfos+SX, iprodione+SX, iprovalicarb+SX, isofetamid+SX, isoflucypram+SX, isoprothiolane+SX, isopyrazam+SX, isotianil+SX, kasugamycin+SX, kresoxim-methyl+SX, laminarin+SX, leaves and bark of Quercus+SX, mancozeb+SX, mandestrobin+SX, mandipropamid+SX, maneb+SX, mefentrifluconazole+SX, mepanipyrim+SX, mepronil+SX, meptyldinocap+SX, metalaxyl+SX, metalaxyl-M+SX, metarylpicoxamid+SX, metconazole+SX, methasulfocarb+SX, metiram+SX, metominostrobin+SX, metrafenone+SX, metyltetraprole+SX, myclobutanil+SX, naftifine+SX, nuarimol+SX, octhilinone+SX, ofurace+SX, orysastrobin+SX, oxadixyl+SX, oxathiapiprolin+SX, oxine-copper+SX, oxolinic acid+SX, oxpoconazole+SX, oxpoconazole fumarate+SX, oxycarboxin+SX, oxytetracycline+SX, pefurazoate+SX, penconazole+SX, pencycuron+SX, penflufen+SX, penthiopyrad+SX, phenamacril+SX, phosphorous acid+SX, phthalide+SX, picarbutrazox+SX, picoxystrobin+SX, piperalin+SX, polyoxins+SX, potassium hydrogencarbonate+SX, potassium dihydrogenphosphite+SX, probenazole+SX, prochloraz+SX, procymidone+SX, propamidine+SX, propamocarb+SX, propiconazole+SX, propineb+SX, proquinazid+SX, prothiocarb+SX, prothioconazole+SX, pydiflumetofen+SX, pyraclostrobin+SX, pyrametostrobin+SX, pyraoxystrobin+SX, pyrapropoyne+SX, pyraziflumid+SX, pyrazophos+SX, pyribencarb+SX, pyributicarb+SX, pyridachlometyl+SX, pyrifenox+SX, pyrimethanil+SX, pyrimorph+SX, pyriofenone+SX, pyrisoxazole+SX, pyroquilon+SX, Quillaja extract+SX, quinconazole+SX, quinofumelin+SX, quinoxyfen+SX, quintozene+SX, Saponins of Chenopodium quinoa+SX, seboctylamine+SX, sedaxane+SX, silthiofam+SX, simeconazole+SX, sodium hydrogencarbonate+SX, spiroxamine+SX, streptomycin+SX, sulfur+SX, tebuconazole+SX, tebufloquin+SX, teclofthalam+SX, tecnazene+SX, terbinafine+SX, tetraconazole+SX, thiabendazole+SX, thifluzamide+SX, thiophanate+SX, thiophanate-methyl+SX, thiram+SX, thymol+SX, tiadinil+SX, tolclofos-methyl+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX, triadimefon+SX, triadimenol+SX, triazoxide+SX, triclopyricarb+SX, tricyclazole+SX, tridemorph+SX, trifloxystrobin+SX, triflumizole+SX, triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX, vinclozolin+SX, yellow mustard powder+SX, zinc thiazole+SX, zineb+SX, ziram+SX, zoxamide+SX, N′-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6)+SX, N′-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6)+SX, N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9)+SX, N′-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9)+SX, N′-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1)+SX, N′-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5)+SX, N′-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3)+SX, N′-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5)+SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6)+SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5)+SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6)+SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8)+SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4)+SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2)+SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6)+SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4)+SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5)+SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[l-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2)+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1)+SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8)+SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4)+SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9)+SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2)+SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8)+SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9)+SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5)+SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1)+SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2)+SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide+SX, N-methoxy-N′-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N′-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N′-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9)+SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate+SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate+SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate+SX, Agrobacterium radiobactor strain K1026+SX, Agrobacterium radiobactor strain K84+SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo (registered trademark) EZ Nematicide)+SX, Bacillus amyloliquefaciens strain AT332+SX, Bacillus amyloliquefaciens strain B3+SX, Bacillus amyloliquefaciens strain D747+SX, Bacillus amyloliquefaciens strain DB101+SX, Bacillus amyloliquefaciens strain DB102+SX, Bacillus amyloliquefaciens strain GB03+SX, Bacillus amyloliquefaciens strain FZB24+SX, Bacillus amyloliquefaciens strain FZB42+SX, Bacillus amyloliquefaciens strain IN937a+SX, Bacillus amyloliquefaciens strain MBI600+SX, Bacillus amyloliquefaciens strain QST713+SX, Bacillus amyloliquefaciens isolate strain B246+SX, Bacillus amyloliquefaciens strain F727+SX, Bacillus amyloliquefaciens subsp. plantarum strain D747+SX, Bacillus licheniformis strain HB-2+SX, Bacillus licheniformis strain SB3086+SX, Bacillus pumilus strain AQ717+SX, Bacillus pumilus strain BUF-33+SX, Bacillus pumilus strain GB34+SX, Bacillus pumilus strain QST2808+SX, Bacillus simplex strain CGF2856+SX, Bacillus subtilis strain AQ153+SX, Bacillus subtilis strain AQ743+SX, Bacillus subtilis strain BU1814+SX, Bacillus subtilis strain D747+SX, Bacillus subtilis strain DB101+SX, Bacillus subtilis strain FZB24+SX, Bacillus subtilis strain GB03+SX, Bacillus subtilis strain HAI0404+SX, Bacillus subtilis strain IAB / BS03+SX, Bacillus subtilis strain MBI600+SX, Bacillus subtilis strain QST30002 / AQ30002+SX, Bacillus subtilis strain QST30004 / AQ30004+SX, Bacillus subtilis strain QST713+SX, Bacillus subtilis strain QST714+SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24+SX, Bacillus subtilis strain Y1336+SX, Burkholderia cepacia+SX, Burkholderia cepacia type Wisconsin strain J82+SX, Burkholderia cepacia type Wisconsin strain M54+SX, Candida oleophila strain O+SX, Candida saitoana+SX, Chaetomium cupreum+SX, Clonostachys rosea+SX, Coniothyrium minitans strain CGMCC8325+SX, Coniothyrium minitans strain CON / M / 91-8+SX, cryptococcus albidus+SX, Erwinia carotovora subsp. carotovora strain CGE234M403+SX, Fusarium oxysporum strain Fo47+SX, Gliocladium catenulatum strain J1446+SX, Paenibacillus polymyxa strain AC-1+SX, Paenibacillus polymyxa strain BS-0105+SX, Pantoea agglomerans strain E325+SX, Phlebiopsis gigantea strain VRA1992+SX, Pseudomonas aureofaciens strain TX-1+SX, Pseudomonas chlororaphis strain 63-28+SX, Pseudomonas chlororaphis strain AFS009+SX, Pseudomonas chlororaphis strain MA342+SX, Pseudomonas fluorescens strain 1629RS+SX, Pseudomonas fluorescens strain A506+SX, Pseudomonas fluorescens strain CL145A+SX, Pseudomonas fluorescens strain G7090+SX, Pseudomonas sp. strain CAB-02+SX, Pseudomonas syringae strain 742RS+SX, Pseudomonas syringae strain MA-4+SX, Pseudozyma flocculosa strain PF-A22UL+SX, Pseudomonas rhodesiae strain HAI-0804+SX, Pythium oligandrum strain DV74+SX, Pythium oligandrum strain M1+SX, Streptomyces griseoviridis strain K61+SX, Streptomyces lydicus strain WYCD108US+SX, Streptomyces lydicus strain WYEC108+SX, Talaromyces flavus strain SAY-Y-94-01+SX, Talaromyces flavus strain V117b+SX, Trichoderma asperellum strain ICC012+SX, Trichoderma asperellum SKT-1+SX, Trichoderma asperellum strain T25+SX, Trichoderma asperellum strain T34+SX, Trichoderma asperellum strain TV1+SX, Trichoderma atroviride strain CNCM 1-1237+SX, Trichoderma atroviride strain LC52+SX, Trichoderma atroviride strain IMI 206040+SX, Trichoderma atroviride strain SC1+SX, Trichoderma atroviride strain SKT-1+SX, Trichoderma atroviride strain T11+SX, Trichoderma gamsii strain ICC080+SX, Trichoderma harzianum strain 21+SX, Trichoderma harzianum strain DB104+SX, Trichoderma harzianum strain DSM 14944+SX, Trichoderma harzianum strain ESALQ-1303+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain ITEM908+SX, Trichoderma harzianum strain kd+SX, Trichoderma harzianum strain MO1+SX, Trichoderma harzianum strain SF+SX, Trichoderma harzianum strain T22+SX, Trichoderma harzianum strain T39+SX, Trichoderma harzianum strain T78+SX, Trichoderma harzianum strain TH35+SX, Trichoderma polysporum strain IMI206039+SX, trichoderma stromaticum+SX, Trichoderma virens strain G-41+SX, Trichoderma virens strain GL-21+SX, Trichoderma viride+SX, Variovorax paradoxus strain CGF4526+SX, Harpin protein+SX.

[1483] Combination of the Present ingredient in the above Group (c) and the Present compound X:

[1484] 1-methylcyclopropene+SX, 1,3-diphenylurea+SX, 2,3,5-triiodobenzoic acid+SX, IAA ((1H-indol-3-yl)acetic acid)+SX, IBA (4-(1H-indol-3-yl)butyric acid)+SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid)+SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid)+SX, 4-CPA (4-chlorophenoxyacetic acid)+SX, 5-aminolevulinic acid hydrochloride+SX, 6-benzylaminopurine+SX, abscisic acid+SX, AVG (aminoethoxyvinylglycine)+SX, anisiflupurin+SX, ancymidol+SX, butralin+SX, calcium carbonate+SX, calcium chloride+SX, calcium formate+SX, calcium peroxide+SX, calcium polysulfide+SX, calcium sulfate+SX, chlormequat-chloride+SX, chlorpropham+SX, choline chloride+SX, cloprop+SX, cyanamide+SX, cyclanilide+SX, daminozide+SX, decan-1-ol+SX, dichlorprop+SX, dikegulac+SX, dimethipin+SX, diquat+SX, ethephon+SX, ethychlozate+SX, flumetralin+SX, flurprimidol+SX, forchlorfenuron+SX, formononetin+SX, Gibberellin A+SX, Gibberellin A3+SX, inabenfide+SX, Kinetin+SX, lipochitooligosaccharide SP104+SX, maleic hydrazide+SX, mefluidide+SX, mepiquat-chloride+SX, oxidized glutathione+SX, paclobutrazol+SX, pendimethalin+SX, prohexadione-calcium+SX, prohydrojasmon+SX, pyraflufen-ethyl+SX, sintofen+SX, sodium 1-naphthaleneacetate+SX, sodium cyanate+SX, thidiazuron+SX, triapenthenol+SX, tribufos+SX, trinexapac-ethyl+SX, uniconazole-P+SX, 2-(naphthalen-1-yl)acetamide+SX, [4-oxo-4-(2-phenylethyl)amino]butylate+SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate+SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol+SX, Claroideoglomus etunicatum+SX, Claroideoglomus claroideum+SX, Funneliformis mosseae+SX, Gigaspora margarita+SX, Gigaspora rosea+SX, Glomus aggregatum+SX, Glomus deserticola+SX, Glomus monosporum+SX, Paraglomus brasillianum+SX, Rhizophagus clarus+SX, Rhizophagus intraradices RTI-801+SX, Rhizophagus irregularis DAOM 197198+SX, Azorhizobium caulinodans+SX, Azospirillum amazonense+SX, Azospirillum brasilense XOH+SX, Azospirillum brasilense Ab-V5+SX, Azospirillum brasilense Ab-V6+SX, Azospirillum caulinodans+SX, Azospirillum halopraeferens+SX, Azospirillum irakense+SX, Azospirillum lipoferum+SX, Bradyrhizobium elkanii SEMIA 587+SX, Bradyrhizobium elkanii SEMIA 5019+SX, Bradyrhizobium japonicum TA-11+SX, Bradyrhizobium japonicum USDA 110+SX, Bradyrhizobium liaoningense+SX, Bradyrhizobium lupini+SX, Delftia acidovorans RAY209+SX, Mesorhizobium ciceri+SX, Mesorhizobium huakii+SX, Mesorhizobium loti+SX, Rhizobium etli+SX, Rhizobium galegae+SX, Rhizobium leguminosarum bv. Phaseoli+SX, Rhizobium leguminosarum bv. Trifolii+SX, Rhizobium leguminosarum bv. Viciae+SX, Rhizobium trifolii+SX, Rhizobium tropici+SX, Sinorhizobium fredii+SX, Sinorhizobium meliloti+SX, Zucchini Yellow Mosaik Virus weak strain+SX.

[1485] Combination of the Present ingredient in the above Group (d) and the Present compound X:

[1486] anthraquinone+SX, deet+SX, icaridin+SX.

[1487] The ratio of the Present compound X to the Present ingredient includes, but not limited thereto, as a ratio by weight (the Present compound X:the Present ingredient) 1,000:1 to 1:1,000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the others.

[1488] The Present compound X has control effect on harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Examples of the harmful arthropods, harmful nematodes, and harmful mollusks include the followings.Hemiptera:

[1489] from the family Delphacidae, for example, small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), cereal leafhopper (Javesella pellucida), sugarcane leafhopper (Perkinsiella saccharicida), and Tagosodes orizicolus;

[1490] from the family Cicadellidae, for example, green rice leafhopper (Nephotettix cincticeps), green paddy leafhopper (Nephotettix virescens), rice leafhopper (Nephotettix nigropictus), zigzag-striped leafhopper (Recilia dorsalis), tea green leafhopper (Empoasca onukii), potato leafhopper (Empoasca fabae), corn leafhopper (Dalbulus maidis), rice leafhopper (Cofana spectra), and Amrasca biguttula biguttula;

[1491] from the family Aphrophoridae, for example, European spittlebug (Philaenus spumarius);

[1492] from the family Cercopidae, for example, Mahanarva posticata and Mahanarva fimbriolata;

[1493] from the family Aphididae, for example, bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), green apple aphid (Aphis pomi), apple aphid (Aphis spiraecola), green peach aphid (Myzus persicae), leaf-curling plum aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rosy apple aphid(Dysaphis plantaginea), false cabbage aphid (Lipaphis erysimi), potato aphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), grain aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), brown citrus aphid (Toxoptera citricida), mealy plum aphid (Hyalopterus pruni), cane aphid (Melanaphis sacchari), black rice root aphid (Tetraneura nigriabdominalis), sugarcane cottony aphid (Ceratovacuna lanigera), apple woolly aphid (Eriosoma lanigerum), and English grain aphid (Sitobion avenae);

[1494] from the family Phylloxeridae, for example, grapevine phylloxera (Daktulosphaira vitifoliae), Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), and Southern pecan leaf phylloxera (Phylloxera russelae);

[1495] from the family Adelgidae, for example, hemlock woolly aphid (Adelges tsugae), balsam woolly aphid (Adelges piceae), and Aphrastasia pectinatae;

[1496] from the family Pentatomidae, for example, black rice bug (Scotinophara lurida), black paddy bug (Scotinophara coarctata), common green stink bug (Nezara antennata), white-spotted spined bug (Eysarcoris aeneus), lewis spined bug (Eysarcoris lewisi), white-spotted bug (Eysarcoris ventralis), Eysarcoris annamita, brown marmorated stink bug (Halyomorpha halys), green plant bug (Nezara viridula), brown stink bug(Euschistus heros), red banded stink bug(Piezodorus guildinii), Oebalus pugnax, and Dichelops melacanthus; from the family Cydnidae, for example, Scaptocoris castanea;

[1497] from the family Alydidae, for example, bean bug (Riptortus clavatus), corbett rice bug (Leptocorisa chinensis), and rice bug (Leptocorisa acuta);

[1498] from the family Coreidae, for example, Cletus punctiger and Australian leaf-footed bug (Leptoglossus australis);

[1499] from the family Lygaeidae, for example, oriental chinch bug (Cavelerius saccharivorus), seed bug (Togo hemipterus), and chinch bug (Blissus leucopterus);

[1500] from the family Miridae, for example, rice leaf bug (Trigonotylus caelestialium), sorghum plant bug (Stenotus rubrovittatus), wheat leaf bug (Stenodema calcarata), and American tarnished plant bug (Lygus lineolaris);

[1501] from the family Aleyrodidae, for example, greenhouse whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthus spiniferus), tea spiny whitefly (Aleurocanthus camelliae), and Pealius euryae;

[1502] from the family Diaspididae, for example, Abgrallaspis cyanophylli, red scale (Aonidiella aurantii), San José scale (Diaspidiotus perniciosus), white peach scale (Pseudaulacaspis pentagona), arrowhead scale (Unaspis yanonensis), and citrus snow scale (Unaspis citri);

[1503] from the family Coccidae, for example, pink wax scale (Ceroplastes rubens);

[1504] from the family Margarodidae, for example, fluted scale (Icerya purchasi) and seychelles fluted scale (Icerya seychellarum);

[1505] from the family Pseudococcidae, for example, solanum mealybug (Phenacoccus solani), cotton mealybug (Phenacoccus solenopsis), Japanese mealybug (Planococcus kraunhiae), white peach scale (Pseudococcus comstocki), citrus mealybug (Planococcus citri), currant mealybug (Pseudococcus calceolariae), long-tailed mealybug (Pseudococcus longispinus), and tuttle mealybug (Brevennia rehi);

[1506] from the family Psyllidae, for example, citrus psylla (Diaphorina citri), two-spotted citrus psyllid (Trioza erytreae), pear sucker (Cacopsylla pyrisuga), Cacopsylla chinensis, potato psyllid (Bactericera cockerelli), and Pear psylla (Cacopsylla pyricola);

[1507] from the family Tingidae, for example, sycamore lace bug (Corythucha ciliata), aster tingid (Corythucha marmorata), Japanese pear lace bug (Stephanitis nashi), and azalea lace bug (Stephanitis pyrioides);

[1508] from the family Cimicidae, for example, common bed bug (Cimex lectularius) and tropical bed bug(Cimex hemipterus);

[1509] from the family Cicadidae, for example, Quesada gigas;

[1510] from the family Reduviidae, for example, Triatoma infestans, large kissing bug (Triatoma rubrofasciata), Triatoma dimidiata, and Rhodonius prolixus; and the others.Lepidoptera:

[1511] from the family Crambidae, for example, rice stem borer (Chilo suppressalis), Dark-headed stem borer (Chilo polychrysus), white stem borer (Scirpophaga innotata), yellow paddy borer (Scirpophaga incertulas), Rupela albina, rice leaf roller (Cnaphalocrocis medinalis), Marasmia patnalis, rice leaf roller (Marasmia exigua), cotton leaf roller (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), cabbage webworm (Hellula undalis), grape leafroller (Herpetogramma luctuosale), bluegrass webworm (Parapediasia teterrellus), rice case-worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), and eggplant fruit borer (Leucinodes orbonalis);

[1512] from the family Pyralidae, for example, lesser cornstalk borer (Elasmopalpus lignosellus), mealworm moth (Plodia interpunctella), persimmon bark borer (Euzophera batangensis), and fig moth (Cadra cautella);

[1513] from the family Noctuidae, for example, cotton worm (Spodoptera litura), beet armyworm (Spodoptera exigua), rice armyworm (Mythimna separata), cabbage moth (Mamestra brassicae), pink borer (Sesamia inferens), grass armyworm (Spodoptera mauritia), green rice caterpillar (Naranga aenescens), Spodoptera frugiperda, true armyworm (Spodoptera exempta), semitropical armyworm (Spodoptera eridania), black cutworm (Agrotis ipsilon), beet worm (Autographa nigrisigna), rice looper (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia spp., Heliothis spp. (such as tobacco budworm (Heliothis virescens)), Helicoverpa spp. (such as tobacco budworm (Helicoverpa armigera), corn earworm (Helicoverpa zea)), velvet-bean caterpillar (Anticarsia gemmatalis), cotton leafworm (Alabama argillacea), and hop vine borer (Hydraecia immanis);

[1514] from the family Pieridae, for example, common cabbage worm (Pieris rapae);

[1515] from the family Tortricidae, for example, oriental fruit moth (Grapholita molesta), Grapholita dimorpha, soybean moth (Leguminivora glycinivorella), Matsumuraeses azukivora, summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai), Japanese tea tortrix (Homona magnanima), apple tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), sugarcane shoot borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), and European grapevine moth (Lobesia botrana);

[1516] from the family Gracillariidae, for example, tea leaf roller (Caloptilia theivora) and Asiatic apple leaf miner (Phyllonorycter ringoniella);

[1517] from the family Carposinidae, for example, peach fruit moth (Carposina sasakii);

[1518] from the family Lyonetiidae, for example, coffee leaf miner (Leucoptera coffeella), peach leaf miner (Lyonetia clerkella), and Lyonetia prunifoliella;

[1519] from the family Lymantriidae, for example, Lymantria spp. (such as gypsy moth (Lymantria dispar)) and Euproctis spp. (such as tea lymantriid (Euproctis pseudoconspersa));

[1520] from the family Plutellidae, for example, diamondback moth (Plutella xylostella);

[1521] from the family Gelechiidae, for example, peach worm (Anarsia lineatella), sweetpotato leaf folder (Helcystogramma triannulella), pink bollworm (Pectinophora gossypiella), potato moth (Phthorimaea operculella), and Tuta absoluta;

[1522] from the family Arctiidae, for example, American white moth (Hyphantria cunea);

[1523] from the family Castniidae, for example, giant sugarcane borer (Telchin licus);

[1524] from the family Cossidae, for example, Cossus insularis;

[1525] from the family Geometridae, for example, Ascotis selenaria;

[1526] from the family Limacodidae, for example, blue-striped nettle grub (Parasa lepida);

[1527] from the family Stathmopodidae, for example, persimmon fruit moth (Stathmopoda masinissa);

[1528] from the family Sphingidae, for example, tobacco hornworm (Acherontia lachesis);

[1529] from the family Sesiidae, for example, Nokona feralis, cherry borer (Synanthedon hector), and Synanthedon tenuis;

[1530] from the family Hesperiidae, for example, rice skipper (Parnara guttata);

[1531] from the family Tineidae, for example, casemaking clothes moth (Tinea translucens), common clothes moth (Tineola bisselliella);and the others.Thysanoptera:

[1532] from the family Thripidae, for example, western flower thrips (Frankliniella occidentalis), oriental thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), eastern flower thrips (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis), Echinothrips americanus, and avocado thrips (Scirtothrips perseae);

[1533] from the family Phlaeothripidae, for example, aculeated rice thrips (Haplothrips aculeatus);and the others.Diptera:

[1534] from the family Anthomyiidae, for example, seedcorn maggot (Delia platura), onion maggot (Delia antiqua), and beet leaf miner (Pegomya cunicularia);

[1535] from the family Ulidiidae, for example, sugarbeet root maggot (Tetanops myopaeformis);

[1536] from the family Agromyzidae, for example, rice leaf miner (Agromyza oryzae), tomato leaf miner (Liriomyza sativae), chrysanthemum leaf miner (Liriomyza trifolii), and pea leafminer (Chromatomyia horticola);

[1537] from the family Chloropidae, for example, rice stem maggot (Chlorops oryzae);

[1538] from the family Tephritidae, for example, melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), Malaysian fruit fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), Queensland fruit fly (Bactrocera tryoni), Mediterranean fruit fly (Ceratitis capitata), apple maggot (Rhagoletis pomonella), and Japanese cherry fruit fly (Rhacochlaena japonica);

[1539] from the family Ephydridae, for example, smaller rice leaf miner (Hydrellia griseola), whorl maggot (Hydrellia philippina), and paddy stem maggot (Hydrellia sasakii);

[1540] from the family Drosophilidae, for example, cherry drosophila (Drosophila suzukii), and common fruit fly (Drosophila melanogaster);

[1541] from the family Phoridae, for example, Megaselia spiracularis;

[1542] from the family Psychodidae, for example, Clogmia albipunctata;

[1543] from the family Sciaridae, for example, Bradysia difformis;

[1544] from the family Cecidomyiidae, for example, hessian fly (Mayetiola destructor) and paddy gall fly (Orseolia oryzae);

[1545] from the family Diopsidae, for example, Diopsis macrophthalma;

[1546] from the family Glossinidae, for example, Glossina palpalis and Glossina morsitans;

[1547] from the family Simuliidae, for example, Simulium japonicum and Simulium damnosum;

[1548] from the subfamily Phlebotominae;

[1549] from the family Tipulidae, for example, rice crane fly (Tipula aino), common cranefly (Tipula oleracea), and European cranefly (Tipula paludosa);

[1550] from the family Culicidae, for example, southern house mosquito (Culex pipiens pallens), Culex tritaeniorhynchus, Culex pipiens f. molestus, brown house mosquito (Culex quinquefasciatus), northern house mosquito (Culex pipiens pipiens), Culex vishnui, Asian tiger mosquito (Aedes albopictus), dengue mosquito (Aedes aegypti), Chinese malaria mosquito (Anopheles sinensis), Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, and Anopheles minimus;

[1551] from the family Simulidae, for example, Prosimulium yezoensis and Simulium ornatum;

[1552] from the family Tabanidae, for example, Tabanus trigonus;

[1553] from the family Muscidae, for example, house fly (Musca domestica), false stable fly (Muscina stabulans), biting house fly (Stomoxys calcitrans), and buffalo fly (Haematobia irritans);

[1554] from the family Calliphoridae;

[1555] from the family Sarcophagidae;

[1556] from the family Chironomidae, for example, Chironomus plumosus, Chironomus yoshimatsui, and Glyptotendipes tokunagai;

[1557] from the family Fannidae;and the others.Coleoptera:

[1558] from the family Chrysomelidae, for example, Diabrotica spp. (such as western corn rootworm (Diabrotica virgifera virgifera), southern corn rootworm (Diabrotica undecimpunctata howardi), northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), banded cucumber beetle (Diabrotica balteata), cucurbit beetle(Diabrotica speciosa)), bean leaf beetle (Cerotoma trifurcata), barley leaf beetle (Oulema melanopus), cucurbit leaf beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), cabbage flea beetle (Phyllotreta cruciferae), western black flea beetle (Phyllotreta pusilla), cabbage stem flea beetle (Psylliodes chrysocephala), hop flea beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flea beetle (Chaetocnema pulicaria), sweet-potato flea beetle (Chaetocnema confinis), potato flea beetle (Epitrix cucumeris), rice leaf beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), Laccoptera quadrimaculata, and tobacco flea beetle (Epitrix hirtipennis);

[1559] from the family Carabidae, for example, Seedcorn beetle (Stenolophus lecontei) and slender seed-corn ground beetle (Clivina impressifrons);

[1560] from the family Scarabaeidae, for example, cupreus chafer (Anomala cuprea), soybean beetle (Anomala rufocuprea), Anomala albopilosa, Japanese beetle (Popillia japonica), yellowish elongate chafer (Heptophylla picea), European Chafer(Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., Phyllophaga spp. (such as June beetle (Phyllophaga crinita)), and Diloboderus spp. (such as Diloboderus abderus);

[1561] from the family Anthriibidae, for example, coffee bean weevil(Araecerus coffeae);

[1562] from the family Aponidae, for example, sweet-potato weevil (Cylas formicarius);

[1563] from the family Bruchidae, for example, Mexican bean weevil (Zabrotes subfasciatus);

[1564] from the family Scolytidae, for example, pine beetle (Tomicus piniperda) and coffee berry borer (Hypothenemus hampei);

[1565] from the family Curculionidae, for example, West Indian sweet-potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize wevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), grain weevil (Sitophilus granarius), rice plant weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), Rhabdoscelus lineaticollis, boll weevil (Anthonomus grandis), nunting billbug (Sphenophorus venatus), southern corn billbug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rusty gourd-shaped weevil (Scepticus griseus), brown gourd-shaped weevil (Scepticus uniformis), Aracanthus spp. (such as Aracanthus mourei), and cotton root borer (Eutinobothrus brasiliensis);

[1566] from the family Tenebrionidae, for example, red meal beetle (Tribolium castaneum), mason beetle (Tribolium confusum), and lesser mealworm (Alphitobius diaperinus);

[1567] from the family Coccinellidae, for example, twenty-eight-spotted ladybird (Epilachna vigintioctopunctata);

[1568] from the family Bostrychidae, for example, common powder-post beetle (Lyctus brunneus), and lesser grain borer (Rhizopertha dominica);

[1569] from the family Ptinidae;

[1570] from the family Cerambycidae, for example, citrus long-horned beetle (Anoplophora malasiaca), Migdolus fryanus, and peach borer (Aromia bungii);

[1571] from the family Elateridae, for example, Melanotus okinawensis, barley wireworm (Agriotes fuscicollis), Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., and Aeolus spp.;

[1572] from the family Staphylinidae, for example, Paederus fuscipes;

[1573] from the family Dermestidae, for example, varied carpet beetle (Anthrenus verbasci), hide beetle (Dermestes maculates), and khapra beetle (Trogoderma granarium);

[1574] from the family Anobiidae, for example, tobacco beetle (Lasioderma serricorne), and biscuit beetle (Stegobium paniceum);

[1575] from the family Laemophloeidae, for example, flat grain beetle (Cryptolestes ferrugineus);

[1576] from the family Silvanidae, for example, saw-toothed grain beetle (Oryzaephilus surinamensis);

[1577] from the family Nitidulidae, for example, blossom beetle (Brassicogethes aeneus);and the others.Orthoptera:

[1578] from the family Acrididae, for example, oriental migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian plague locust (Chortoicetes terminifera), red locust (Nomadacris septemfasciata), brown locust(Locustana pardalina), tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), differential grasshopper (Melanoplus differentialis), two-striped grasshopper (Melanoplus bivittatus), migratory grasshopper (Melanoplus sanguinipes), red-legged grasshopper (Melanoplus femurrubrum), clear-winged grasshopper (Camnula pellucida), desert locust (Schistocerca gregaria), Yellow-winged locust(Gastrimargus musicus), spur-throated locust (Austracris guttulosa), Japanese grasshopper (Oxya yezoensis), rice grasshopper (Oxya japonica), and Bombay locust (Patanga succincta);

[1579] from the family Gryllotalpidae, for example, oriental mole cricket (Gryllotalpa orientalis);

[1580] from the family Gryllidae, for example, house cricket (Acheta domestica), and emma field cricket (Teleogryllus emma);

[1581] from the family Tettigoniidae, for example, mormon cricket (Anabrus simplex);and the others.Hymenoptera:

[1582] from the family Tenthredinidae, for example, beet sawfly (Athalia rosae) and nippon cabbage sawfly (Athalia japonica);

[1583] from the family Formicidae, for example, Solenopsis spp. (such as red imported fire ant (Solenopsis invicta), tropical fire ant (Solenopsis geminata)), Atta spp. (such as brown leaf-cutting ant (Atta capiguara), Acromyrmex spp., Paraponera clavata, black house ant (Ochetellus glaber), little red ant (Monomorium pharaonis), Argentine ant (Linepithema humile), Formica japonica, Pristomyrmex punctutus, Pheidole noda, big-headed ant (Pheidole megacephala), Camponotus spp. (such as Camponotus japonicus, Camponotus obscuripes), Pogonomyrmex spp. (such as western harvester ant (Pogonomyrmex occidentalis)), Wasmania spp. (such as Wasmania auropunctata), and long-legged ant (Anoplolepis gracilipes);

[1584] from the family Vespidae, for example, Asian giant hornet (Vespa mandarinia, Vespa simillima, Vespa analis, Asian hornet(Vespa velutina), and Polistes jokahamae;

[1585] from the family Siricidae, for example, pine wood wasp (Urocerus gigas);

[1586] from the family Bethylidae;and the others.Blattodea:

[1587] from the family Ectobiidae, for example, German cockroach (Blattella germanica);

[1588] from the family Blattidae, for example, smoky-brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australasiae), brown cockroach (Periplaneta brunnea), and black cockroach (Blatta orientalis);

[1589] from the family Termitidae, for example, Japanese termite (Reticulitermes speratus), Formosan termite (Coptotermes formosanus), western drywood termite (Incisitermes minor), Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans; and the others.Siphonaptera:

[1590] from the family Pulicidae, for example, human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), oriental rat flea (Xenopsylla cheopis), and chicken flea (Echidnophaga gallinacea); from the family Pulicidae, for example, chigoe flea (Tunga penetrans);

[1591] from the family Ceratophyllidae, for example, European rat flea (Nosopsyllus fasciatus);

[1592] and the others.Psocodae:

[1593] from the family Pediculidae, for example, head louse (Pediculus humanus capitis);

[1594] from the family Pthiridae, for example, crab louse (Pthirus pubis);

[1595] from the family Haematopinidae, for example, short-nosed cattle louse (Haematopinus eurysternus) and pig louse (Haematopinus suis);

[1596] from the family Linognathidae, for example, blue cattle louse (Linognathus vituli), sheep face louse (Linognathus ovillus), and capillate louse (Solenopotes capillatus);

[1597] from the family Bovicoliidae, for example, cattle biting louse (Bovicola bovis), sheep biting louse (Bovicola ovis), Bovicola breviceps, Damalinia forficula, and Werneckiella spp.;

[1598] from the family Trichodectidae, for example, dog biting louse (Trichodectes canis) and cat louse (Felicola subrostratus);

[1599] from the family Menoponidae, for example, common chicken louse (Menopon gallinae), chicken body louse (Menacanthus stramineus), and Trinoton spp.;

[1600] from the family Trimenoponidae, for example, Cummingsia spp.;

[1601] from the family Trogiidae, for example, death watch (Trogium pulsatorium);

[1602] from the family Liposcelidae or Liposcelididae, for example, book louse (Liposcelis corrodens), Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila; and the other.Thysanura:

[1603] from the family Lepismatidae, for example, oriental silverfish (Ctenolepisma villosa) and moth fish (Lepisma saccharina);and the others.Acari:

[1604] from the family Tetranychidae, for example, common red spider mite (Tetranychus urticae), kanzawa spider mite (Tetranychus kanzawai), red spider mite (Tetranychus evansi), citrus red mite (Panonychus citri), fruit-tree red spider mite (Panonychus ulmi), and Oligonychus spp.;

[1605] from the family Eriophyidae, for example, Japanese citrus rust mite (Aculops pelekassi), Phyllocoptruta citri, tomato mite (Aculops lycopersici), purple mite (Calacarus carinatus), tea rust mite (Acaphylla theavagrans), Eriophyes chibaensis, apple bud mite (Aculus schlechtendali), Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.;

[1606] from the family Tarsonemidae, for example, broad mite (Polyphagotarsonemus latus);

[1607] from the family Tenuipalpidae, for example, Brevipalpus phoenicis;

[1608] from the family Tuckerellidae;

[1609] from the family Ixodidae, for example, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, American dog tick (Dermacentor variabilis), Dermacentor taiwanensis, Rocky Mountain wood tick (Dermacentor andersoni), netted tick (Dermacentor reticulatus), Ixodes ovatus, Ixodes persulcatus, black-legged tick (Ixodes scapularis), Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, lone star tick (Amblyomma americanum), gulf coast tick (Amblyomma maculatum), Rhipicephalus microplus, cattle tick (Rhipicephalus annulatus), brown dog tick (Rhipicephalus sanguineus), Rhipicephalus appendiculatus, and Rhipicephalus decoloratus;

[1610] from the family Argasidae, for example, fowl tick (Argas persicus), Ornithodoros hermsi, and Ornithodoros turicata;

[1611] from the family Acaridae, for example, cereal mite (Tyrophagus putrescentiae) and grassland mite (Tyrophagus similis);

[1612] from the family Pyroglyphidae, for example, American house dust mite (Dermatophagoides farinae) and European house dust mite (Dermatophagoides pteronyssinus);

[1613] from the family Cheyletidae, for example, Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, and Cheyletiella yasguri;

[1614] from the family Psoroptidae, for example, sheep scab mite (Psoroptes ovis), horse psoroptic mange mite (Psoroptes equi), Knemidocoptes mutans, ear mange mite (Otodectes cynotis), and Chorioptes spp.;

[1615] from the family Sarcoptidae, for example, Notoedres cati, Notoedres muris, and itch mite (Sarcoptes scabiei);

[1616] from the family Listrophoridae, for example, Listrophorus gibbus;

[1617] from the family Dermanyssidae, for example, bird mite (Dermanyssus gallinae);

[1618] from the family Macronyssidae, for example, feather mite (Ornithonyssus sylviarum) and tropical rat mite (Ornithonyssus bacoti);

[1619] from the family Varroidae, for example, Varroa jacobsoni;

[1620] from the family Demodicidae, for example, dog follicle mite (Demodex canis) and cat follicle mite (Demodex cati);

[1621] from the family Trombiculidae, for example, Leptotrombidium akamushi, Leptotrombidium pallidum, and Leptotrombidium scutellare;and the others.Araneae:

[1622] from the family Eutichuridae, for example, Cheiracanthium japonicum;

[1623] from the family Theridiidae, for example, red-back spider (Latrodectus hasseltii);and the others.Polydesmida:

[1624] from the family Paradoxosomatidae, for example, flat-backed millipede (Oxidus gracilis) and Nedyopus tambanus; and the others.Isopoda:

[1625] from the family Armadillidiidae, for example, common pill bug (Armadillidium vulgare);and the others.Chilopoda:

[1626] from the family Scutigeridae, for example, Thereuonema hilgendorfi;

[1627] from the family Scolopendridae, for example, giant tropical centipede (Scolopendra subspinipes);

[1628] from the family Ethopolyidae, for example, Bothropolys rugosus; and the others.Gastropoda:

[1629] from the family Limacidae, for example, tree slug (Limax marginatus) and garden tawny slug (Limax flavus);

[1630] from the family Philomycidae, for example, Meghimatium bilineatum;

[1631] from the family Ampullariidae, for example, golden apple snail (Pomacea canaliculata);

[1632] from the family Lymnaeidae, for example, Austropeplea ollula; and the others.Nematoda:

[1633] from the family Aphelenchoididae, for example, rice white-tip nematode (Aphelenchoides besseyi);

[1634] from the family Pratylenchidae, for example, root lesion nematode (Pratylenchus coffeae), Pratylenchus brachyurus, California meadow nematode (Pratylenchus neglectus), and Radopholus similis;

[1635] from the family Heteroderidae, for example, javanese root-knot nematode (Meloidogyne javanica), southern root-knot nematode (Meloidogyne incognita), guava root-knot nematodes (Meloidogyne enterolobii), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera rostochiensis), and white potato cyst nematode (Globodera pallida);

[1636] from the family Hoplolaimidae, for example, Rotylenchulus reniformis;

[1637] from the family Anguinidae, for example, strawberry bud nematode (Nothotylenchus acris), and stem nematode (Ditylenchus dipsaci);

[1638] from the family Tylenchulidae, for example, citrus nematode (Tylenchulus semipenetrans);

[1639] from the family Longidoridae, for example, dagger nematode (Xiphinema index);

[1640] from the family Trichodoridae;

[1641] from the family Parasitaphelenchidae, for example, pine wilt disease (Bursaphelenchus xylophilus);and the others.

[1642] The harmful arthropods such as harmful insects and harmful mites, harmful mollusks, and harmful nematodes may be those having a reduced susceptibility to or a developed resistance to an insecticide, a miticide, a molluscicide, or a nematicide.

[1643] The method for controlling harmful arthropods of the present invention is carried out by applying an effective amount of the Present compound, the Present compound X, or the Composition A to a harmful arthropod directly and / or a habitat thereof (for example, plant bodies, soil, an interior of a house, animal bodies). Examples of the method for controlling harmful arthropods of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoking treatment, water surface treatment, and seed treatment.

[1644] The Present compound, the Present compound X, or the Composition A is usually used by mixing it with inert carrier(s) such as solid carrier(s), liquid carrier(s), and gaseous carrier(s), surfactant(s), and the like, and as needed, adding thereto auxiliary agent(s) for formulation such as binder(s), dispersant(s), and stabilizer(s) to be formulated into an aqueous suspension formulation, an oily suspension formulation, an oil solution, an emulsifiable concentrate, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a granular wettable powder, a dust formulation, a granule, a tablet, an aerosol formulation, a resin formulation, or the like. In addition to these formulations, the Present compound, the Present compound X, or the Composition A may be used by formulating it into a dosage form described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271-276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.

[1645] These formulations usually comprise 0.0001 to 99% by weight ratio of the Present compound, the Present compound X, or the Composition A.

[1646] Examples of the solid carrier include fine powders and granules of clays (for example, pyrophyllite clay and kaolin clay), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid white clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride), and the others; as well as resins (for example, polypropylene, polyester, polyurethane, polyamide, and polyvinyl chloride).

[1647] Examples of the liquid carrier include water, alcohols (for example, ethanol, cyclohexanol, benzyl alcohol, propylene glycol, and polyethylene glycol), ketones (for example, acetone and cyclohexanone), aromatic hydrocarbons (for example, xylene, phenyl xylyl ethane, and methylnaphthalene), aliphatic hydrocarbons (for example, hexane and cyclohexane), esters (for example, ethyl acetate, methyl oleate, and propylene carbonate), nitriles (for example, acetonitrile), ethers (for example, ethylene glycol dimethyl ether), amides (for example, N,N-dimethylformamide and N,N-dimethyloctanamide), sulfoxides (for example, dimethyl sulfoxide), lactams (for example, N-methylpyrrolidone and N-octylpyrrolidone), fatty acids (for example, oleic acid), and vegetable oils (for example, soybean oil).

[1648] Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[1649] Examples of the surfactant include nonionic surfactants (for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters), and anionic surfactants (for example, alkyl sulfonates, alkyl aryl sulfonates, and alkyl sulfates). The specific examples thereof include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[1650] Examples of the other auxiliary agent for formulation include binders, dispersants, colorants, and stabilizers, and the specific examples thereof include polysaccharides (for example, starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids), acidic isopropyl phosphate, and dibutylhydroxytoluene.

[1651] As used herein, examples of the plant include whole plant, stem and leaf, flower, ear, fruit, tree stem, branch, crown, seed, vegetative reproductive organ, and seedling.

[1652] A vegetative reproductive organ means a part of plant such as root, stem, and leaf which has a growth capability even when said part is separated from the plant body and placed into soil. Examples of the vegetative reproductive organ include tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. Stolon is also referred to as “runner”, and propagule is also referred to as “propagulum” and categorized into broad bud and bulbil. Vine cutting means a shoot (collective term of leaf and stem) of sweet potato, glutinous yam, or the like. Bulb, corm or solid bulb, tuber, rhizome, cane cuttings, rhizophore, and tuberous root are also collectively referred to as “bulb”. For example, cultivation of potato starts with planting a tuber into soil, and the tuber to be used is generally referred to as “seed potato”.

[1653] Examples of a method for controlling harmful arthropods by applying an effective amount of the Present compound, the Present compound X, or the Composition A to soils include a method of applying an effective amount of the Present compound, the Present compound X, or the Composition A to soil before planting plants or after planting plants, a method of applying an effective amount of the Present compound, the Present compound X, or the Composition A to a root part of a crop to be protected from damage such as ingestion by harmful arthropods, and a method of controlling harmful arthropods that ingest a plant by permeating and transferring an effective amount of the Present compound, the Present compound X, or the Composition A from a root into the interior of the plant body. Specifically, examples of the application method include planting hole treatment (for example, spraying into planting holes and soil mixing after planting hole treatment), plant foot treatment (for example, plant foot spraying, soil mixing after plant foot treatment, irrigation at plant foot, and plant foot treatment at a later seeding raising stage), planting furrow treatment (for example, planting furrow spraying and soil mixing after planting furrow treatment), planting row treatment (for example, planting row spraying, soil mixing after planting row treatment, and planting row spraying at a growing stage), planting row treatment at the time of sowing (for example, planting row spraying at the time of sowing and soil mixing after planting row treatment at the time of sowing), broadcast treatment (for example, overall soil surface spraying and soil mixing after broadcast treatment), side-article treatment, treatment of water surface (for example, application to water surface and application to water surface after flooding), other soil spraying treatment (for example, spraying of a granular formulation on leaves at a growing stage, spraying under a canopy or around a tree stem, spraying on the soil surface, mixing with surface soil, spraying into seed holes, spraying on the ground surfaces of furrows, and spraying between plants), other irrigation treatment (for example, soil irrigation, irrigation at a seedling raising stage, chemical solution injection treatment, irrigation of a plant part just above the ground, chemical solution drip irrigation, and chemigation), seedling raising box treatment (for example, spraying into a seedling raising box, irrigation of a seedling raising box, and flooding into a seedling raising box with chemical solution), seedling raising tray treatment (for example, spraying on a seedling raising tray, irrigation of a seedling raising tray, and flooding into a seedling raising tray with chemical solution), seedbed treatment (for example, spraying on a seedbed, irrigation of a seedbed, spraying on a lowland rice nursery, and immersion of seedlings), seedbed soil incorporation treatment (for example, mixing with seedbed soil, mixing with seedbed soil before sowing, spraying at sowing before covering with soils, spraying at sowing after covering with soils, and mixing with covering with soils), and other treatment (for example, mixing with culture soil, plowing under, mixing with surface soil, mixing with soil at the place where raindrops fall from a canopy, treatment at a planting position, spraying of a granule formulation on flower clusters, and mixing with a paste fertilizer).

[1654] Examples of the application to seeds (or seed treatments) include an application of the Present compound, the Present compound X, or the Composition A to seeds or vegetative reproductive organs, and specific examples thereof include spraying treatment in which a suspension of the Present compound, the Present compound X, or the Composition A is sprayed onto seed surface or the vegetative reproductive organ surface in the form of mist; smearing treatment in which the Present compound, the Present compound X, or the Composition A is coated on a surface of seeds or the vegetative reproductive organs; a soaking treatment in which the seeds or vegetative reproductive organs are soaked into the solution of the Present compound, the Present compound X, or the Composition A for a certain time; and a method for coating the seeds or the vegetative reproductive organs with a carrier containing the Present compound, the Present compound X, or the Composition A (for example, film coating treatment and pellet coating treatment). Examples of the above-described vegetative reproductive organ include particularly seed potato.

[1655] When the Composition A is applied to seeds or vegetative reproductive organs, the Composition A may be also applied to seeds or vegetative reproductive organs as a single formulation, or the Composition A may be applied to seeds or vegetative reproductive organs as multiple different formulations by multiple times. Examples of the method in which the Composition A is applied as multiple different formulations by multiple times include, for example, a method in which the formulations comprising as an active component the Present compound or the Present compound X only are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredient: and a method in which the formulations comprising as an active component the Present compound or the Present compound X and the Present ingredients are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredients other than the already-applied Present ingredients, are included.

[1656] As used herein, seeds or vegetative reproductive organs holding the Present compound, the Present compound X, or the Composition A mean seeds or vegetative reproductive organs in the state where the Present compound, the Present compound X, or the Composition A is adhered to a surface of the seeds or the vegetative reproductive organs. The above-described seeds or vegetative reproductive organs holding the Present compound, the Present compound X, or the Composition A may be adhered by any other materials that are different from the Present compound, the Present compound X, or the Composition A before or after being adhered the Present compound, the Present compound X, or the Composition A to the seeds or vegetative reproductive organs.

[1657] Also, when the Composition A is adhered in a form of layer(s) to a surface of seeds or vegetative reproductive organs, the layer(s) is / are composed of one layer or a multiple layers. Also, when multiple layers are formed, each of the layer may be composed of a layer comprising one or more active ingredients, or a combination of a layer comprising one or more active ingredients and a layer not comprising an active ingredient.

[1658] Seeds or vegetative reproductive organs holding the Present compound, the Present compound X, or the Composition A can be obtained, for example, by applying the formulations comprising the Present compound, the Present compound X, or the Composition A by the above-described application method to seeds or vegetative reproductive organs.

[1659] When the Present compound, the Present compound X, or the Composition A is applied for harmful arthropods control in agricultural fields, the application dose thereof is usually within a range of 1 to 10,000 g of the Present compound or the Present compound X per 10,000 m2. In the case of being applied to seeds or vegetative reproductive organs, the application dose thereof is usually within a range of 0.001 to 100 g of the Present compound or the Present compound X per 1 Kg of seeds or vegetative reproductive organs. When the Present compound, the Present compound X, or the Composition A is formulated into an emulsifiable concentrate, a wettable powder, or a flowable, etc., they are usually applied by diluting them with water so as to make an effective concentration of the active ingredients 0.01 to 10,000 ppm, and the granular formulation, the dust formulation, or the like is usually applied as itself without diluting them.

[1660] Also, the resin preparation of the Present compound X or the Composition A which is processed into a sheet or a string may be applied by winding a plant with a sheet or a string of the resin preparation, putting a string of the resin preparation around a crop so that the plant is surrounded by the string, or laying a sheet of the resin preparation on the soil surface near the root of a plant.

[1661] When the Present compound, the Present compound X, or the Composition A is used to control harmful arthropods that live inside a house, the application dose as an amount of the Present compound or the Present compound X is usually within a range from 0.01 to 1,000 mg per 1 m2 of an area to be treated, in the case of using it on a planar area. In the case of using it spatially, the application dose as an amount of the Present compound or the Present compound X is usually within a range from 0.01 to 500 mg per 1 m3 of the space to be treated. When the Present compound, the Present compound X, or the Composition A is formulated into emulsifiable concentrates, wettable powders, flowables, or the others, such formulations are usually applied after diluting them with water in such a way that a concentration of the active ingredient is within a range from 0.1 to 10,000 ppm. In the case of being formulated into oil solutions, aerosols, smoking agents, poison baits, and the others, such formulations are used as themselves without diluting them.

[1662] When the Present compound, the Present compound X, or the Composition A is used for controlling external parasites of livestock such as cows, horses, pigs, sheep, goats, and chickens and small animals such as dogs, cats, rats, and mice, the composition of the present invention may be applied to the animals by a known method in the veterinary field. Specifically, when systemic control is intended, the composition of the present invention is administered to the animals as a tablet, a mixture with feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous, and intraperitoneal injections). On the other hand, when non-systemic control is intended, the composition of the present invention is applied to the animals by means of spraying of the oil solution or aqueous solution, pour-on or spot-on treatment, washing of the animals with a shampoo formulation, or by putting a collar or ear tag made of the resin formulations to the animals. In the case of being administered to an animal body, the dose of the Present compound or the Present compound X is usually within a range from 0.1 to 1,000 mg per 1 kg of an animal body weight.

[1663] Also, the Present compound, the Present compound X, or the Composition A may be used as an agent for controlling harmful arthropods in agricultural lands such as fields, paddy fields, turfs, and orchards. Examples of the plants include the followings.

[1664] corn (dent corn, flint corn, flour corn, popcorn, waxy corn, sweet corn, and field corn), rice (long grain rice, short grain rice, medium grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, and glutinous rice), wheat (bread wheat (hard wheat, soft wheat, medium wheat, red wheat, and white wheat), durum wheat, spelt wheat, and club wheat, winter wheat and spring wheat of them), barley (two-rowed barley (=barley for brewery), six-rowed barley, hull-less barley, and pearl barley, winter barley and spring barley of them), rye (winter rye and spring rye), triticale (winter triticale and spring triticale), oat (winter oat and spring oat), sorghum, cotton (upland cotton and Pima cotton), soybean (ripe seed harvest soybean, green soybeans, and early harvest soybeans, indeterminate type, determinate type, and semi-determinate type of them), peanut, buckwheat, beet (beets for sugar production, beets for feed, beets for root vegetable, beets for leaf vegetable, and beets for fuel), rapeseed (winter rapeseed and spring rapeseed), canola (winter canola and spring canola), sunflower (sunflowers for oil extraction, edible sunflowers, and sunflowers for ornamental purpose), sugar cane, tobacco, tea, mulberry, solanaceous vegetables (for example, eggplant, tomato, pimento, pepper, and potato), cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, water melon, and melon), cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, and cauliflower), asteraceous vegetables (for example, burdock, crown daisy, artichoke, and lettuce), liliaceous vegetables (for example, welsh onion, onion, garlic, and asparagus), ammiaceous vegetables (for example, carrot, parsley, celery, and parsnip), chenopodiaceous vegetables (for example, spinach and Swiss chard), lamiaceous vegetables (for example, perilla, mint, and basil), strawberry, sweet potato, glutinous yam, eddoe, pomaceous fruits (for example, apple, pear, Japanese pear, Chinese white pear, Chinese quince, and quince), stone fleshy fruits (for example, peach, plum, nectarine, Japanese apricot (Prunus mume), cherry fruit, apricot, and prune), citrus fruits (for example, Citrus unshiu, orange, lemon, lime, and grapefruit), nuts (for example, chestnuts, walnuts, hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts), berry fruits (for example, blueberry, cranberry, blackberry, and raspberry), grapes, Japanese persimmon, fig, olive, Japanese plum, banana, coffee, date palm, coconuts, ornamental plants, forest plants, turfs, grasses, and the others.

[1665] The above plants are not specifically limited as long as they are generally cultivated cultivars. The above plants also include plants which may be produced by natural breeding, plants which may be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of the genetically modified crops include plants which have resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, or herbicide such as bromoxynil and dicamba; plants which can synthesize a selective toxin known in Bacillus spp. such as Bacillus thuringiensis or the like; and plants which can synthesize a gene fragment or the like which is partially identical to an endogenous gene derived from a harmful insect, and induce a gene silencing (RNAi; RNA interference) in the target harmful insect to achieve a specific insecticidal activity.EXAMPLES

[1666] Hereinafter, the present invention is illustrated more in detail by Preparation Examples, Formulation Examples, Test Examples, and the like, but the present invention is not limited to these Examples only.

[1667] In the present description, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, t-Bu represents a tert-butyl group, C2F5 represents a perfluoroethyl group, c-Pr represents a cyclopropyl group, Bn represents a benzyl group, Ph represents a phenyl group, Py2 represents a 2-pyridyl group, Py3 represents a 3-pyridyl group, and Py4 represents a 4-pyridyl group. When c-Pr, Ph, Py2, Py3, and Py4 have substituent(s), the substituent(s) is / are indicated before the symbols with the substitution position(s). For example, 1-CN-c-Pr represents a 1-cyanocyclopropyl group, 3,4-F2-Ph represents a 3,4-difluorophenyl group, 2-C2F5-Ph represents a 2-(perfluoroethyl)phenyl group, 4-SO2CF3-Ph represents a 4-(trifluoromethanesulfonyl)phenyl group, 3,4-(OCF3)2-Ph represents a 3,4-bis(trifluoromethoxy)phenyl group, 3-SCF3-4-OCF3-Ph represents a 3-[(trifluoromethyl)thio]-4-(trifluoromethoxy)phenyl group, and 4-CF3—Py2 represents a 4-(trifluoromethyl)-2-pyridyl group.

[1668] First, Preparation Examples of the Present compounds X and the preparation intermediate compounds thereof are shown below.

[1669] When a physical property of a compound is measured by liquid chromatography / mass spectrometry (hereinafter referred to as “LCMS”), the measured molecular ion value [M+H]+ or [M−H]−, and retention time (hereinafter referred to as “RT”) are described. The conditions of liquid chromatography (hereinafter referred to as “LC”) are as follows.[LC Conditions]Column: L-column2 ODS, inner diameter: 4.6 mm, length: 30 mm, particle size: 3 μm (Chemicals Evaluation and Research Institute, Japan)

[1671] UV measurement wavelength: 254 nm

[1672] Mobile phase: Solution A: 0.1% formic acid in water,

[1673] Solution B: 0.1% formic acid in acetonitrile

[1674] Flow rate: 2.0 mL / min

[1675] Gradient conditions: sending a solution with the concentration gradient described in Table LC1.

[1676] TABLE LC1TimeSolution ASolution B(min)(%)(%)0.0190102.0001004.0001004.019010Reference Preparation Example 1

[1677] To a mixture of 6-bromo-3-(ethylthio)imidazo[1,2-a]pyridine-2-amine (hereinafter referred to as “Intermediate compound Z”) (1.1 g) prepared according to the method described in WO 2018 / 052136 pamphlet and THF (8 mL) was added 4-(trifluoromethyl)benzoyl chloride (0.83 g), then triethylamine (1.1 mL) was added thereto, and the resulting mixture was stirred at room temperature for 30 minutes. To the resulting mixture was added water, and the resulting mixture was subjected to extraction with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the Intermediate compound 1 represented by the following formula (1.4 g).

[1678]

[1679] Intermediate compound 1: 1H-NMR (CDCl3) δ: 9.39 (1H, s), 8.52 (1H, s), 8.07 (2H, d), 7.79 (2H, d), 7.57 (1H, d), 7.47 (1H, d), 2.75 (2H, q), 1.24 (3H, t).Reference Preparation Example 2

[1680] A mixture of the Intermediate compound Z (6.12 g), 3-(trifluoromethylthio)benzoic acid (5.0 g), 4-(dimethylamino)pyridine (0.55 g), pyridine (50 mL), and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (6.47 g) was stirred at 100° C. for 2 hours. To the resulting mixture was added water, and the resulting mixture was subjected to extraction with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the Intermediate compound 2 represented by the following formula (6.57 g).

[1681]

[1682] Intermediate compound 2: 1H-NMR (CDCl3) δ: 8.56-8.53 (2H, m), 8.24 (1H, s), 8.10 (1H, d), 7.87 (1H, d), 7.60 (1H, t), 7.54 (1H, d), 7.39 (1H, d), 2.77 (2H, q), 1.25 (3H, t).Reference Preparation Example 2-1

[1683] The compounds prepared according to the Reference Preparation Example 2 and physical properties thereof are shown below.A Compound Represented by Formula (A-1)

[1684] wherein the combination of A2, A3, A4, A5, G4, and R3b represents any one combination indicated in Table A-1.

[1685] TABLE A-1IntermediatecompoundA2A3A4A5G4R3b3C-SCF3CHCHCHCHCF34C-SCF3CHCHCHCHCl5C-SCF3CHCHCHNBr6CHC-SCF3CHCHCHBr7CHC-SCF3CHCHCHI8CHC-SCF3CHCHNH12C-lCHCHCHCHBr13CHC-BrCHCHCHBr14CHC-OCF3CHCHCHCl15CHC-CHCHCHClOCH2CF 316CHC-CNCHCHCHBr17C-CF3CHC-CF3CHCHI18C-CF3CHC-CNCHCHBr19C-CF3CHC-BrCHCHI20C-BrCHC-BrCHCHI21C-BrCHNCHCHI22C-ClCHC-ClCHCHI23C-OCF3CHC-FCHCHBr24C-FC-CNCHCHCHBr25C-FC-FCHCHCHBr

[1686] Intermediate compound 3: 1H-NMR (CDCl3) δ: 8.56 (1H, s), 8.38 (1H, s), 8.23 (1H, s), 8.09 (1H, t), 7.89 (1H, d), 7.85-7.40 (3H, m), 2.78 (2H, q), 1.18 (3H, t).

[1687] Intermediate compound 4: 1H-NMR (CDCl3) δ: 8.63-8.61 (2H, m), 8.23 (1H, s), 8.08 (1H, d), 7.87 (1H, d), 7.75-7.48 (3H, m), 2.76 (2H, q), 1.19 (3H, t).

[1688] Intermediate compound 5: 1H-NMR (CDCl3) δ: 8.62 (1H, s), 8.53 (1H, d), 8.34 (1H, d), 7.76-7.46 (3H, m), 7.31-7.29 (1H, m), 2.64 (2H, q), 1.19 (3H, t).

[1689] Intermediate compound 6: 1H-NMR (CDCl3) δ: 8.53 (1H, s), 8.34 (1H, s), 7.99 (2H, d), 7.80 (2H, d), 7.56 (1H, d), 7.39 (1H, d), 2.75 (2H, q), 1.24 (3H, t).

[1690] Intermediate compound 7: 1H-NMR (CDCl3) δ: 8.57 (1H, s), 8.44 (1H, s), 7.99 (2H, d), 7.79 (2H, d), 7.70-7.42 (2H, m), 2.73 (2H, q), 1.23 (3H, t).

[1691] Intermediate compound 8: 1H-NMR (CDCl3) δ: 8.53 (1H, s), 8.36 (1H, s), 8.12-8.09 (1H, m), 7.84 (2H, d), 7.68 (2H, d), 6.92-6.90 (1H, m), 3.22 (2H, q), 1.32 (3H, t). Intermediate compound 12: 1H-NMR (CDCl3) δ: 8.52 (1H, s), 8.45 (1H, s), 8.29 (1H, s), 7.91-7.88 (2H, m), 7.52 (1H, d), 7.37 (1H, d), 7.25-7.20 (1H, m), 2.75 (2H, q), 1.23 (3H, t).

[1692] Intermediate compound 13: 1H-NMR (CDCl3) δ: 8.53 (1H, s), 8.34 (1H, s), 7.84 (2H, d), 7.69 (2H, d), 7.56 (1H, d), 7.35 (1H, d), 2.75 (2H, q), 1.24 (3H, t).

[1693] Intermediate compound 14: 1H-NMR (CDCl3) δ: 8.56 (1H, s), 8.35 (1H, s), 7.95 (2H, d), 7.65 (1H, d), 7.54 (2H, d), 7.35 (1H, d), 2.76 (2H, q), 1.23 (3H, t).

[1694] Intermediate compound 15: 1H-NMR (CDCl3) δ: 8.63 (1H, s), 8.44 (1H, s), 7.97 (2H, d), 7.61 (1H, d), 7.51 (2H, d), 7.31 (1H, d), 4.48-4.36 (2H, m), 2.75 (2H, q), 1.19 (3H, t).

[1695] Intermediate compound 16: 1H-NMR (CDCl3) δ: 8.63 (1H, s), 8.54 (1H, s), 8.07 (2H, d), 7.82 (2H, d), 7.55 (1H, d), 7.40 (1H, d), 2.76 (2H, q), 1.17 (3H, t).

[1696] Intermediate compound 17: 1H-NMR (CDCl3) δ: 8.65 (1H, s), 8.41-8.37 (2H, m), 8.09 (1H, s), 7.92 (1H, s), 7.51 (1H, d), 7.45 (1H, d), 2.78 (2H, q), 1.25 (3H, t).

[1697] Intermediate compound 18: 1H-NMR (CDCl3) δ: 8.54 (1H, s), 8.43-8.41 (2H, m), 8.11 (1H, s), 7.93-7.87 (1H, m), 7.53 (1H, d), 7.41 (1H, d), 2.77 (2H, q), 1.26 (3H, t).

[1698] Intermediate compound 19: 1H-NMR (CDCl3) δ: 8.70-8.46 (1H, m), 8.64 (1H, s), 8.28 (1H, s), 8.12 (1H, s), 7.96 (1H, s), 7.54-7.48 (1H, m), 7.45-7.38 (1H, m), 2.77 (2H, q), 1.24 (3H, t).

[1699] Intermediate compound 20: 1H-NMR (CDCl3) δ: 8.63 (1H, s), 8.27-8.22 (1H, m), 7.99 (2H, d), 7.87 (1H, t), 7.53-7.48 (1H, m), 7.44 (1H, d), 2.75 (2H, q), 1.24 (3H, t).

[1700] Intermediate compound 21: 1H-NMR (CDCl3) δ: 9.05-9.04 (1H, m), 8.87 (1H, d), 8.64-8.62 (1H, m), 8.45-8.40 (2H, m), 7.51 (1H, dd), 7.44 (1H, d), 2.75 (2H, q), 1.24 (3H, t).

[1701] Intermediate compound 22: 1H-NMR (CDCl3) δ: 8.64-8.61 (1H, m), 8.31-8.26 (1H, m), 7.82-7.78 (2H, m), 7.57 (1H, t), 7.50 (1H, dd), 7.44 (1H, d), 2.75 (2H, q), 1.33-1.19 (3H, m).

[1702] Intermediate compound 23: 1H-NMR (CDCl3) δ: 8.55-8.54 (1H, m), 8.21 (1H, s), 7.63-7.56 (3H, m), 7.41 (1H, d), 7.20 (1H, d), 2.77 (2H, q), 1.26 (3H, t).

[1703] Intermediate compound 24: 1H-NMR (CDCl3) δ: 8.54 (1H, s), 8.43 (1H, s), 7.85-7.82 (3H, m), 7.56 (1H, d), 7.42 (1H, d), 2.77 (2H, q), 1.25 (3H, t).

[1704] Intermediate compound 25: 1H-NMR (CDCl3) δ: 8.53-8.53 (1H, m), 8.30 (1H, s), 7.86-7.81 (1H, m), 7.72-7.70 (1H, m), 7.56 (1H, d), 7.40 (1H, d), 7.35-7.28 (1H, m), 2.75 (2H, q), 1.24 (3H, t).

[1705] A compound represented by formula (A-1) wherein the combination of A2, A3, A4, A5, G4, and R3b represents any one combination indicated in Table AA-1.

[1706] TABLE AA-1IntermediatecompoundA2A3A4A5G4R3b41CHC-CF3CHCHCHI43C-CF3CHCHNCHBr44CHCHC-CF3NCHBr45C-CF3CHCHNCHI46C-BrC-FCHCHCHCF347C-CF3CHC-ICHCHI48C -CF3NCHCHCHI50CHC-ClCHCHCHI51C-ClCHCHCHCHI52CHC-C2F5CHCHCHI53C-ICHC-ICHCHI54CHC-OCF3CHCHCHBr55C-OCF3CHCHCHCHBr56CHC-OCF2HCHCHCHBr57C-OCF2HCHCHCHCHBr58CHC-CF3CHCHCHCF359CHC-SCF3CHCHCHCF360CHC-CF3CHCHCHCl61CHC-SCF3CHCHCHCl62C-CF3CHC-CF3CHCHCF363C-FC-FC-FCHCHI64C-OCF2HCHC-OCF2HCHCHI65C-ClC-OCF2HCHCHCHI66CHC-SF5CHCHCHI

[1707] Intermediate compound 41: 1H-NMR (CDCl3) δ: 8.63 (1H, s), 8.34 (1H, s), 8.06 (2H, d), 7.79 (2H, d), 7.47 (2H, dd), 2.74 (2H, q), 1.23 (3H, t).

[1708] Intermediate compound 43: 1H-NMR (CDCl3) δ: 10.48 (1H, s), 8.88 (1H, d), 8.59 (1H, s), 8.53 (1H, d), 7.75 (1H, d), 7.60 (1H, d), 7.37 (1H, dd), 2.74 (2H, q), 1.24 (3H, t).

[1709] Intermediate compound 44: 1H-NMR (CDCl3) δ: 10.48 (1H, s), 8.58-8.53 (2H, m), 8.15 (1H, t), 7.90 (1H, d), 7.59 (1H, d), 7.39-7.35 (1H, m), 2.73 (2H, q), 1.27 (3H, t).

[1710] Intermediate compound 45: 1H-NMR (CDCl3) δ: 10.49 (1H, s), 8.88 (1H, d), 8.64-8.60 (2H, m), 7.75 (1H, dd), 7.50-7.49 (2H, m), 2.74 (2H, q), 1.24 (3H, t).

[1711] Intermediate compound 46: 1H-NMR (DMSO-D6) δ: 10.79 (1H, s), 8.92 (1H, s), 8.36 (1H, dd), 8.10-8.07 (1H, m), 7.86 (1H, d), 7.69 (1H, dd), 7.58 (1H, t), 2.81 (2H, q), 1.08 (3H, t).

[1712] Intermediate compound 47: 1H-NMR (CDCl3) δ: 8.65-8.64 (1H, m), 8.45-8.43 (2H, m), 8.14 (1H, s), 7.51 (1H, dd), 7.42 (1H, dd), 4.34 (1H, br s), 2.77 (2H, q), 1.24 (3H, t).

[1713] Intermediate compound 48: LCMS: 493 [M+H]+, RT=1.897 min Intermediate compound 50: 1H-NMR (DMSO-D6) δ: 10.62 (1H, s), 8.76 (1H, s), 8.02 (2H, d), 7.63 (3H, d), 7.56 (1H, dd), 2.77 (2H, q), 1.08 (3H, t).

[1714] Intermediate compound 51: 1H-NMR (DMSO-D6) δ: 10.66 (1H, s), 8.76-8.76 (1H, m), 8.04-8.04 (1H, m), 7.97 (1H, d), 7.71-7.70 (1H, m), 7.65-7.55 (3H, m), 2.77 (2H, q), 1.08 (3H, t).

[1715] Intermediate compound 52: 1H-NMR (CDCl3) δ: 8.63-8.62 (1H, m), 8.37 (1H, br s), 8.08 (2H, d), 7.77 (2H, d), 7.52-7.44 (2H, m), 2.74 (2H, q), 1.24 (3H, t)

[1716] Intermediate compound 53: 1H-NMR (CDCl3) δ: 8.64-8.63 (1H, m), 8.26-8.25 (1H, m), 8.21-8.20 (3H, m), 7.52-7.42 (2H, m), 2.75 (2H, q), 1.24 (3H, t)

[1717] Intermediate compound 54: 1H-NMR (DMSO-D6) δ: 10.66 (1H, s), 8.76 (1H, d), 8.13 (2H, d), 7.64 (1H, d), 7.58-7.54 (3H, m), 2.77 (2H, q), 1.08 (3H, t).

[1718] Intermediate compound 55: 1H-NMR (DMSO-D6) δ: 10.75 (1H, s), 8.77 (1H, d), 8.06 (1H, d), 7.94 (1H, s), 7.71 (1H, t), 7.66-7.64 (2H, m), 7.57 (1H, dd), 2.78 (2H, q), 1.08 (3H, t).

[1719] Intermediate compound 56: 1H-NMR (DMSO-D6) δ: 10.56 (1H, s), 8.76 (1H, d), 8.08 (2H, d), 7.63 (1H, d), 7.56 (1H, dd), 7.40 (1H, t), 7.33 (2H, d), 2.77 (2H, q), 1.08 (3H, t).

[1720] Intermediate compound 57: 1H-NMR (DMSO-D6) δ: 10.64 (1H, s), 8.77 (1H, s), 7.90 (1H, d), 7.78 (1H, s), 7.65-7.53 (3H, m), 7.44 (1H, d), 7.35 (1H, t), 2.78 (2H, q), 1.10-1.06 (3H, m).

[1721] Intermediate compound 58: 1H-NMR (DMSO-D6) δ: 10.90 (1H, s), 8.93 (1H, s), 8.20 (2H, d), 7.95 (2H, d), 7.86 (1H, d), 7.70 (1H, dd), 2.81 (2H, q), 1.09 (3H, t).

[1722] Intermediate compound 59: 1H-NMR (DMSO-D6) δ: 10.91 (1H, s), 8.93 (1H, s), 8.20 (2H, d), 7.95 (2H, d), 7.86 (1H, d), 7.70 (1H, d), 2.81 (2H, q), 1.09 (3H, t).

[1723] Intermediate compound 60: 1H-NMR (DMSO-D6) δ: 10.79 (1H, s), 8.73 (1H, dd), 8.19 (2H, d), 7.94 (2H, d), 7.70 (1H, dd), 7.50 (1H, dd), 2.78 (2H, q), 1.08 (3H, t).

[1724] Intermediate compound 61: 1H-NMR (DMSO-D6) δ: 10.75 (1H, s), 8.73 (1H, dd), 8.10 (2H, d), 7.90 (2H, d), 7.70 (1H, dd), 7.50 (1H, dd), 2.77 (2H, q), 1.08 (3H, t).

[1725] Intermediate compound 62: 1H-NMR (CDCl3) δ: 8.79-8.77 (1H, m), 8.48-8.44 (1H, br m), 8.41-8.39 (2H, m), 8.10 (1H, s), 7.75 (1H, d), 7.51-7.49 (1H, m), 2.81 (2H, q), 1.27 (3H, t).

[1726] Intermediate compound 63: 1H-NMR (CDCl3) δ: 8.63-8.62 (1H, m), 8.25-8.19 (1H, br s), 7.61 (2H, t), 7.53-7.43 (2H, m), 2.74 (2H, q), 1.23 (3H, t).

[1727] Intermediate compound 64: 1H-NMR (CDCl3) δ: 8.64-8.63 (1H, m), 8.57-8.54 (1H, br s), 7.56-7.56 (2H, m), 7.51-7.40 (2H, m), 7.12-7.11 (1H, m), 6.79-6.42 (2H, m), 2.75 (2H, q), 1.24 (3H, t).

[1728] Intermediate compound 65: 1H-NMR (CDCl3) δ: 8.63-8.62 (1H, m), 8.56-8.53 (1H, br s), 8.08-8.08 (1H, m), 7.87-7.84 (1H, m), 7.51-7.39 (2H, m), 7.35 (1H, d), 6.81-6.45 (1H, m), 2.74 (2H, q), 1.23 (3H, t).

[1729] Intermediate compound 66: 1H-NMR (CDCl3) δ: 8.63-8.63 (1H, m), 8.41-8.38 (1H, br s), 8.05 (2H, d), 7.91 (2H, d), 7.52-7.43 (2H, m), 2.74 (2H, q), 1.23 (3H, t).Reference Preparation Example 3

[1730] To a mixture of the Intermediate compound 1 (500 mg) and chloroform (5 mL) was added mCPBA (purity: 70%, comprising 30% of water) (830 mg) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the resulting mixture were sequentially added a saturated aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium thiosulfate, and the resulting mixture was subjected to extraction with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to give the Intermediate compound 26 (260 mg).

[1731]

[1732] Intermediate compound 26: 1H-NMR (CDCl3) δ: 9.83 (1H, s), 8.78 (1H, s), 8.10 (2H, d), 7.82 (2H, d), 7.74 (1H, d), 7.60 (1H, d), 3.32 (2H, q), 1.36 (3H, t).Reference Preparation Example 3-1

[1733] The compounds prepared according to the Reference Preparation Example 3 and physical properties thereof are shown below.A Compound Represented by Formula (A-2)

[1734] wherein the combination of A2, A3, A4, A5, and R3b represents any one combination indicated in Table A-2.

[1735] TABLE A-2Intermediate compoundA2A3A4A5R3b27C—SCF3CHCHCHBr28CHC—SCF3CHCHBr29CHC—C2F5CHC—FBr42CHC—CF3CHCHI

[1736] Intermediate compound 27: 1H-NMR (CDCl3) δ: 9.78 (1H, s), 8.80-8.76 (1H, m), 8.27 (1H, s), 8.07 (1H, d), 7.89 (1H, d), 7.72 (1H, d), 7.64-7.57 (2H, m), 3.33 (2H, q), 1.36 (3H, t).

[1737] Intermediate compound 28: 1H-NMR (CDCl3) δ: 9.80 (1H, s), 8.77 (1H, s), 8.02 (2H, d), 7.81 (2H, d), 7.72 (1H, d), 7.59 (1H, d), 3.32 (2H, q), 1.36 (3H, t).

[1738] Intermediate compound 29: 1H-NMR (CDCl3) δ: 10.09 (1H, s), 8.84-8.82 (1H, m), 8.36 (1H, t), 7.73 (1H, d), 7.61-7.58 (2H, m), 7.49 (1H, d), 3.32 (2H, q), 1.37 (3H, t).

[1739] Intermediate compound 42: 1H-NMR (CDCl3) δ: 9.83 (1H, s), 8.86 (1H, S), 8.10 (2H, d), 7.80 (2H, d), 7.71 (1H, dd), 7.62 (11H, d), 3.31 (2H, q), 1.36 (3H, t).Reference Preparation Example 4

[1740] To a mixture of 4-(trifluoromethyl)anthranilic acid (3.00 g) and THF (22 mL) was added dropwise a mixture of triphosgene (1.52 g) and THF (15 mL) under ice-cooling. The resulting mixture was stirred at room temperature for 4 hours. To the resulting mixture was added water, and the resulting mixture was subjected to extraction with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the Intermediate compound 30 represented by the following formula (3.30 g).

[1741]

[1742] Intermediate compound 30: 1H-NMR (DMSO-D6) δ: 11.98 (1H, br s), 8.10 (1H, d), 7.54 (1H, d), 7.37 (1H, s).Reference Preparation Example 4-1

[1743] The compound prepared according to the Reference Preparation Example 4 and physical property thereof are shown below.

[1744]

[1745] Intermediate compound 31: 1H-NMR (DMSO-D6) δ: 9.92 (1H, s), 5.83 (1H, d), 5.80-5.77 (1H, m), 5.26 (1H, d).Reference Preparation Example 5

[1746] To a mixture of the Intermediate compound Z (300 mg) and THF (4 mL) was added dropwise potassium bis(trimethylsilyl)amide (1 mol / L THF solution) (2.2 mL) under nitrogen atmosphere at −78° C., and the resulting mixture was stirred for 30 minutes. To the resulting mixture was added a mixture of the Intermediate compound 30 (254 mg) and THF (4 mL), and the resulting mixture was stirred at room temperature for 30 minutes. To the resulting mixture was added a saturated aqueous solution of ammonium chloride, and the resulting mixture was subjected to extraction with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added hexane, and the precipitated solids were filtered. The resulting solids were washed with hexane, and then dried under reduced pressure to give the Intermediate compound 32 represented by the following formula (491 mg).

[1747]

[1748] Intermediate compound 32: 1H-NMR (CDCl3) δ: 8.54 (1H, dd), 8.35 (1H, s), 7.67 (1H, d), 7.60 (1H, dd), 7.41 (1H, dd), 7.00 (1H, s), 6.98 (1H, d), 5.95 (2H, br s), 2.75 (2H, q), 1.27 (3H, t).Reference Preparation Example 5-1

[1749] The compounds prepared according to the Reference Preparation Example 5 and physical properties thereof are shown below.

[1750]

[1751] Intermediate compound 33: 1H-NMR (CDCl3) δ: 8.53-8.53 (1H, m), 8.33 (1H, s), 7.80 (1H, s), 7.57 (1H, d), 7.50 (1H, dd), 7.39 (1H, dd), 6.78 (1H, d), 6.14 (2H, s), 2.74 (2H, q), 1.26 (3H, t).

[1752]

[1753] Intermediate compound 34: 1H-NMR (CDCl3) δ: 8.61-8.60 (1H, m), 8.28 (1H, s), 7.56 (1H, d), 7.50-7.44 (2H, m), 6.57-6.54 (2H, m), 5.96 (2H, s), 2.71 (2H, q), 1.23 (3H, t).Reference Preparation Example 6

[1754] A mixture of the Intermediate compound 32 (491 mg) and triethyl orthoformate (11 mL) was stirred at 100° C. for 1 hour. The resulting mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The resulting solids were washed with hexane to give the Intermediate compound 35 represented by the following formula (447 mg).

[1755]

[1756] Intermediate compound 35: 1H-NMR (CDCl3) δ: 8.65 (1H, dd), 8.51 (1H, d), 8.20 (1H, s), 8.08 (1H, d), 7.77 (1H, dd), 7.61 (1H, dd), 7.50 (1H, dd), 2.77 (2H, q), 1.18 (3H, t).Reference Preparation Example 6-1

[1757] The compounds prepared according to the Reference Preparation Example 6 and physical properties thereof are shown below.

[1758]

[1759] Intermediate compound 36: 1H-NMR (CDCl3) δ: 8.69-8.67 (1H, m), 8.65-8.64 (1H, m), 8.22 (11H, s), 8.03 (1H, dd), 7.92˜7.90 (1H, m), 7.61 (1H, dd), 7.52-7.49 (1H, m), 2.78 (2H, q), 1.19 (3H, t).

[1760]

[1761] Intermediate compound 37: 1H-NMR (CDCl3) δ: 8.76-8.74 (1H, m), 8.22-8.20 (11H, m), 8.14 (1H, s), 7.85 (1H, d), 7.66 (1H, dd), 7.61 (1H, dd), 7.49 (1H, d), 2.77 (2H, q), 1.19 (3H, t).Reference Preparation Example 7

[1762] The compounds prepared according to the Reference Preparation Example 3 and physical properties thereof are shown below.

[1763]

[1764] Intermediate compound 38: 1H-NMR (CDCl3) δ: 9.06 (1H, dd), 8.47 (1H, d), 8.26 (1H, s), 8.09 (1H, d), 7.78 (1H, dd), 7.73 (1H, dd), 7.68 (1H, dd), 3.56 (2H, q), 1.46 (3H, t).

[1765]

[1766] Intermediate compound 39: 1H-NMP (CDCl3) δ: 9.06-9.05 (1H, m), 8.64-8.63 (1H, m), 8.28 (1H, s), 8.04 (1H, dd), 7.93-7.91 (1H, m), 7.73 (1H, dd), 7.69 (1H, dd), 3.59 (2H, q), 1.47 (3H, t).

[1767]

[1768] Intermediate compound 40: 1H-NMR (CDCl3) δ: 9.14 (1H, dd), 8.20 (1H, s), 8.17-8.15 (1H, m), 7.85 (1H, d), 7.79 (1H, dd), 7.67-7.65 (11H, m), 7.60 (1H, dd), 3.57 (2H, q), 1.46 (3H, t).Preparation Example 1

[1769] To a mixture of the Intermediate compound 1 (1.2 g), cesium carbonate (0.88 g), and DMF (6 mL) was added methyl iodide (0.51 mL) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the resulting mixture was added water, and the resulting mixture was subjected to extraction with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate=1:1) to give the Present compound 1 (810 mg),

[1770]

[1771] Present compound 1: 1H-NMR (CDCl3) δ: 8.30 (1H, s), 7.56 (2H, d), 7.50 (1H, d), 7.44-7.38 (3H, m), 3.55 (3H, s), 2.40 (2H, q), 1.10 (3H, t).Preparation Example 1-1

[1772] The compounds prepared according to the Preparation Example 1 and physical properties thereof are shown below. A compound represented by formula (B-1)

[1773] wherein the combination of A2, A3, A4, A5, G4, R1, R3b and n represents any one combination indicated in Table B-1.

[1774] TABLE B-1PresentcompoundA2A3A4A5G4R1R3bn2C-SCF3CHCHCHCHMeBr03C-SCF3CHCHCHCHEtBr04C-SCF3CHCHCHCHMeCF305C-SCF3CHCHCHCHMeCl06C-SCF3CHCHCHNMeBr07CHC-SCF3CHCHCHMeBr08CHC-SCF3CHCHCHEtBr09CHC-SCF3CHCHCHMeI010CHC-SCF3CHCHNMeH015C-ICHCHCHCHMeBr016CHC-BrCHCHCHMeBr017CHC-OCF3CHCHCHMeCl018CHC-OCH2CF3CHCHCHMeCl019CHC-CNCHCHCHMeBr020C-CF3CHC-CF3CHCHMeI021C-CF3CHC-CNCHCHMeBr022C-CF3CHC-BrCHCHMeI023C-BrCHC-BrCHCHMeI024C-BrCHNCHCHMeI025C-ClCHC-ClCHCHMeI026C-OCF3CHC-FCHCHMeBr027C-FC-CNCHCHCHMeBr028C-FC-FCHCHCHMeBr032C-SCF3CHCHCHCHMeBr233C-SCF3CHCHCHCHEtBr238CHC-SCF3CHCHCHMeBr244CHC-C2F5CHC-FCHMeBr2

[1775] Present compound 2: 1H-NMR (CDCl3) δ: 8.30 (1H, s), 7.70-7.66 (2H, m), 7.56-7.49 (2H, m), 7.41 (1H, d), 7.29-7.27 (1H, m), 3.58 (3H, s), 2.38 (2H, q), 1.11 (3H, t).

[1776] Present compound 3: 1H-NMR (CDCl3) δ: 8.30 (1H, d), 7.71-7.66 (2H, m), 7.55-7.50 (2H, m), 7.41 (1H, d), 7.29-7.27 (1H, m), 4.10 (2H, q), 2.31 (2H, q), 1.34 (3H, t), 1.11 (3H, t).

[1777] Present compound 4: 1H-NMR (CDCl3) δ: 8.51 (1H, s), 7.72-7.69 (2H, m), 7.61 (1H, s), 7.53 (1H, d), 7.48 (1H, d), 7.31-7.30 (1H, m), 3.59 (3H, s), 2.39 (2H, q), 1.11 (3H, t).

[1778] Present compound 5: 1H-NMR (CDCl3) δ: 8.19 (1H, s), 7.69-7.66 (2H, m), 7.56-7.51 (2H, m), 7.29-7.27 (2H, m), 3.56 (3H, s), 2.37 (2H, q), 1.10 (3H, t).

[1779] Present compound 6: 1H-NMR (CDCl3) δ: 8.61 (1H, s), 8.52 (1H, s), 7.68-7.66 (2H, m), 7.54 (1H, d), 7.28-7.25 (1H, m), 3.59 (3H, s), 2.38 (2H, q), 1.10 (3H, t).

[1780] Present compound 7: 1H-NMR (CDCl3) δ: 8.31 (1H, s), 7.53-7.41 (6H, m), 3.56 (3H, s), 2.32 (2H, q), 1.10 (3H, t).

[1781] Present compound 8: 1H-NMR (CDCl3) δ: 8.31 (1H, s), 7.55-7.40 (6H, m), 4.08 (2H, q), 2.23 (2H, q), 1.32 (3H, t), 1.10 (3H, t).

[1782] Present compound 9: 1H-NMR (CDCl3) δ: 8.39 (1H, s), 7.53-7.36 (6H, m), 3.53 (3H, s), 2.29 (2H, q), 1.07 (3H, t).

[1783] Present compound 10: 1H-NMR (CDCl3) δ: 8.51-8.50 (1H, m), 8.07 (1H, d), 7.41-7.36 (4H, m), 6.95-6.93 (1H, m), 3.39 (3H, s), 3.17 (2H, q), 1.27 (3H, t).

[1784] Present compound 15: 1H-NMR (CDCl3) δ: 8.31 (1H, s), 7.90-7.87 (1H, m), 7.56 (1H, d), 7.51 (1H, d), 7.39 (1H, d), 7.31 (1H, d), 6.84 (1H, t), 3.52 (3H, s), 2.37 (2H, q), 1.12 (3H, t).

[1785] Present compound 16: 1H-NMR (CDCl3) δ: 8.31 (1H, s), 7.50 (1H, d), 7.40 (1H, d), 7.32-7.28 (4H, m), 3.53 (3H, s), 2.40 (2H, q), 1.11 (3H, t).

[1786] Present compound 17: 1H-NMR (CDCl3) δ: 8.23 (1H, s), 7.57 (1H, d), 7.51 (2H, d), 7.32 (1H, d), 7.00 (2H, d), 3.55 (3H, s), 2.34 (2H, q), 1.10 (3H, t).

[1787] Present compound 18: 1H-NMR (CDCl3) δ: 8.22 (1H, s), 7.56 (1H, d), 7.45 (2H, d), 7.30 (1H, d), 6.70 (2H, d), 4.28-4.26 (2H, m), 3.54 (3H, s), 2.37 (2H, q), 1.10 (3H, t).

[1788] Present compound 19: 1H-NMR (CDCl3) δ: 8.30 (1H, s), 7.53-7.46 (6H, m), 3.56 (3H, s), 2.47 (2H, q), 1.13 (3H, t).

[1789] Present compound 20: 1H-NMR (CDCl3) δ: 8.38 (1H, s), 7.90-7.87 (2H, m), 7.71 (1H, s), 7.52 (1H, d), 7.38 (1H, d), 3.57 (3H, s), 2.46 (2H, q), 1.11 (3H, t).

[1790] Present compound 21: 1H-NMR (CDCl3) δ: 8.29 (1H, s), 7.91-7.87 (2H, m), 7.74 (1H, s), 7.50 (1H, d), 7.42 (1H, d), 3.56 (3H, s), 2.51 (2H, q), 1.13 (3H, t).

[1791] Present compound 22: 1H-NMR (CDCl3) δ: 8.41 (1H, t), 7.80 (1H, s), 7.60 (2H, d), 7.52 (1H, dd), 7.38 (1H, d), 3.54 (3H, s), 2.46 (2H, q), 1.12 (3H, t).

[1792] Present compound 23: 1H-NMR (CDCl3) δ: 8.45-8.43 (1H, m), 7.54-7.50 (4H, m), 7.39 (1H, d), 3.51 (3H, s), 2.46 (2H, q), 1.13 (3H, t).

[1793] Present compound 24: 1H-NMR (CDCl3) δ: 8.50 (1H, d), 8.41 (1H, dd), 8.34 (1H, d), 8.06 (1H, t), 7.54-7.51 (1H, m), 7.38 (1H, dd), 3.55 (3H, s), 2.47 (2H, q), 1.13 (3H, t).

[1794] Present compound 25: 1H-NMR (CDCl3) δ: 8.44-8.43 (1H, m), 7.52 (1H, dd), 7.39 (1H, d), 7.34-7.32 (2H, m), 7.22-7.20 (1H, m), 3.51 (3H, s), 2.46 (2H, q), 1.13 (3H, t).

[1795] Present compound 26: 1H-NMR (CDCl3) δ: 8.32 (1H, s), 7.50 (1H, d), 7.42 (1H, d), 7.21-7.19 (1H, m), 7.05-7.05 (1H, m), 6.83-6.81 (1H, m), 3.54 (3H, s), 2.46 (2H, q), 1.12 (3H, t).

[1796] Present compound 27: 1H-NMR (CDCl3) δ: 8.33 (1H, s), 7.51 (1H, d), 7.42-7.36 (3H, m), 7.25 (1H, d), 3.55 (3H, s), 2.52 (2H, q), 1.14 (3H, t).

[1797] Present compound 28: 1H-NMR (CDCl3) δ: 8.31 (1H, s), 7.49 (1H, d), 7.40 (1H, d), 7.35-7.32 (1H, m), 7.16-7.12 (1H, m), 6.91-6.88 (1H, m), 3.51 (3H, s), 2.43 (2H, q), 1.11 (3H, t).

[1798] Present compound 32: 1H-NMR (CDCl3) δ: 8.82 (1H, s), 7.88-7.41 (6H, m), 3.53-3.43 (5H, m), 1.38-1.20 (3H, m).

[1799] Present compound 33: 1H-NMR (CDCl3) δ: 8.97 (1H, s), 7.84-7.39 (6H, m), 4.08-3.86 (2H, m), 3.61-3.36 (2H, m), 1.35-1.17 (6H, m).

[1800] Present compound 38: 1H-NMR (CDCl3) δ: 8.92-8.84 (1H, s), 7.75-7.55 (6H, m), 3.56-3.31 (5H, m), 1.42-1.26 (3H, m).

[1801] Present compound 44: 1H-NMR (CDCl3) δ: 9.00 (1H, s), 7.84-7.40 (5H, m), 3.61-3.48 (2H, m), 3.40 (3H, s), 1.49-1.39 (3H, m).

[1802] A compound represented by formula (B-1) wherein the combination of A2, A3, A4, A5, G4, R1, R3b, and n represents any one combination indicated in Table C-1.

[1803] TABLE C-1PresentcompoundA2A3A4A5G4R1R3bn64CHC-CF3CHCHCHMeI065CHC-CF3CHCHCHMeI267C-CF3CHCHNCHMeBr068CHCHC-CF3NCHMeBr073C-CF3CHCHNCHMeI075C-BrC-FCHCHCHMeCF3076C-CF3CHC-ICHCHMeI077C-CF3NCHCHCHMeI078C-CF3CHC-CF3CHCHCH2CNI083CHC-OMeCHCHCHMeI084CHC-ClCHCHCHMeI085C-ClCHCHCHCHMeI086CHC-C2F5CHCHCHMeI087C-C2F5CHCHCHCHMeI089C-ICHC-ICHCHMeI090CHC-OCF3CHCHCHMeBr091C-OCF3CHCHCHCHMeBr092CHC-OCF2HCHCHCHMeBr093C-OCF2HCHCHCHCHMeBr0102CHC-CF3CHCHCHMeCF30103CHC-SCF3CHCHCHMeCF30104CHC-CF3CHCHCHMeCl0105CHC-SCF3CHCHCHMeCl0106CHC-CF3CHCHCHEtBr0107CHC-CF3CHCHCHCH2CPrBr0108CHC-CF3CHCHCHCH2CNBr0113C-CNCHCHCHCHMeBr0114C-CF3CHC-CF3CHCHMeCF30115C-CF3CHC-CF3CHCHMeOMe0116CHC-ClCHCHCHMeBr0117C-ClCHCHCHCHMeBr0118C-FC-FC-FCHCHMeI0119CHC-CF3CHCHCHBnBr0120CHC-CF3CHCHCHCH2Py3Br0121C-OCF2HCHC-OCF2HCHCHMeI0122C-ClC-OCF2HCHCHCHMeI0123CHC-SF5CHCHCHMeI0124C-CF3CHC-CF3CHCHCH2OEtCF30

[1804] Present compound 64: 1H-NMR (CDCl3) δ: 8.40 (1H, s), 7.56 (2H, d), 7.51 (1H, dd), 7.45-7.35 (3H, m), 3.55 (3H, s), 2.39 (2H, q), 1.10 (3H, t).

[1805] Present compound 65: 1H-NMR (CDCl3) δ: 8.98 (1H, s), 7.88-7.49 (6H, m), 3.50-3.40 (5H, m), 1.35 (3H, t).

[1806] Present compound 67: 1H-NMR (CDCl3) δ: 8.36 (1H, s), 8.28 (1H, s), 8.14 (1H, s), 7.44-7.31 (3H, m), 3.62 (3H, s), 2.57 (2H, q), 1.15 (3H, t).

[1807] Present compound 68: 1H-NMR (CDCl3) δ: 8.43 (1H, s), 8.17 (1H, d), 7.90 (1H, t), 7.50 (1H, d), 7.32-7.29 (2H, m), 3.64 (3H, s), 2.65 (2H, q), 1.22 (3H, t).

[1808] Present compound 73: 1H-NMR (CDCl3) δ: 8.47 (1H, s), 8.32-8.26 (1H, m), 8.14 (1H, s), 7.45 (1H, d), 7.35 (1H, d), 7.31 (1H, d), 3.62 (3H, s), 2.57 (2H, q), 1.15 (3H, t).

[1809] Present compound 75: 1H-NMR (CDCl3) δ: 8.55 (1H, s), 7.78 (1H, dd), 7.71 (1H, d), 7.49 (1H, dd), 7.30-7.27 (1H, m), 6.84 (1H, t), 3.54 (3H, s), 2.46 (2H, q), 1.13 (3H, t).

[1810] Present compound 76: 1H-NMR (CDCl3) δ: 8.41 (1H, s), 7.99 (1H, s), 7.78 (1H, s), 7.62 (1H, s), 7.52 (1H, dd), 7.39 (1H, dd), 3.53 (3H, s), 2.46 (2H, q), 1.12 (3H, t).

[1811] Present compound 77: LCMS: 507 [M+H]+, RT=1.97 min

[1812] Present compound 78: 1H-NMR (CDCl3) δ: 8.42-8.41 (1H, m), 7.91-7.89 (2H, m), 7.80-7.78 (1H, m), 7.60-7.57 (1H, m), 7.43-7.40 (1H, m), 4.95 (2H, s), 2.60 (2H, q), 1.18 (3H, t).

[1813] Present compound 83: 1H-NMR (CDCl3) δ: 8.40-8.40 (1H, m), 7.50-7.47 (1H, m), 7.42-7.38 (3H, m), 6.64 (2H, d), 3.72 (3H, s), 3.53 (3H, s), 2.31 (2H, q), 1.07 (3H, t).

[1814] Present compound 84: 1H-NMR (CDCl3) δ: 8.41-8.40 (1H, m), 7.53-7.49 (1H, m), 7.39-7.36 (3H, m), 7.13-7.10 (2H, m), 3.52 (3H, s), 2.38 (2H, q), 1.09 (3H, t).

[1815] Present compound 85: 1H-NMR (CDCl3) δ: 8.41-8.40 (1H, m), 7.54-7.49 (2H, m), 7.40-7.37 (1H, m), 7.23-7.20 (2H, m), 7.06-7.02 (1H, m), 3.52 (3H, s), 2.37 (2H, q), 1.11 (3H, t).

[1816] Present compound 86: 1H-NMR (CDCl3) δ: 8.41-8.40 (1H, m), 7.59-7.57 (2H, m), 7.53-7.51 (1H, m), 7.41-7.37 (3H, m), 3.55 (3H, s), 2.32 (2H, q), 1.08 (3H, t).

[1817] Present compound 87: 1H-NMR (CDCl3) δ: 8.38-8.37 (1H, m), 7.71-7.70 (1H, m), 7.64-7.62 (1H, m), 7.52-7.45 (2H, m), 7.39-7.29 (2H, m), 3.56 (3H, s), 2.37 (2H, q), 1.08 (3H, t).

[1818] Present compound 89: 1H-NMR (CDCl3) δ: 8.45-8.43 (1H, m), 7.89-7.88 (1H, m), 7.73-7.73 (2H, m), 7.54-7.51 (1H, m), 7.41-7.38 (1H, m), 3.50 (3H, s), 2.45 (2H, q), 1.14 (3H, t).

[1819] Present compound 90: 1H-NMR (CDCl3) δ: 8.31 (1H, dd), 7.51-7.48 (3H, m), 7.40 (1H, dd), 6.99 (2H, d), 3.53 (3H, s), 2.33 (2H, q), 1.08 (3H, t).

[1820] Present compound 91: 1H-NMR (DMSO-D6) δ: 8.58 (1H, s), 7.67 (1H, d), 7.60 (1H, d), 7.39 (2H, d), 7.31 (1H, s), 7.09 (1H, s), 3.41 (3H, s), 2.43 (2H, q), 0.96 (3H, t).

[1821] Present compound 92: 1H-NMR (DMSO-D6) δ: 8.59 (1H, s), 7.67 (1H, d), 7.58 (1H, d), 7.35 (2H, d), 7.22 (1H, t), 6.99 (2H, d), 3.38 (3H, s), 2.41 (2H, q), 0.96 (3H, t).

[1822] Present compound 93: 1H-NMR (DMSO-D6) δ: 8.58 (1H, s), 7.66 (1H, d), 7.58 (1H, d), 7.26 (1H, t), 7.16 (1H, d), 7.11-7.04 (2H, m), 7.07 (1H, t), 3.39 (3H, s), 2.42 (2H, q), 0.96 (3H, t).

[1823] Present compound 102: 1H-NMR (DMSO-D6) δ: 8.72 (1H, s), 7.89 (1H, d), 7.72 (1H, dd), 7.56 (2H, d), 7.43 (2H, dt), 3.43 (3H, s), 2.42 (2H, q), 0.98 (3H, t).

[1824] Present compound 103: 1H-NMR (CDCl3) δ: 8.20 (1H, s), 7.56-7.42 (5H, m), 7.31 (1H, m), 3.54 (3H, s), 2.29 (2H, q), 1.08 (3H, t).

[1825] Present compound 104: 1H-NMR (DMSO-D6) δ: 8.56 (1H, s), 7.73 (1H, t), 7.54 (3H, dt), 7.42 (2H, t), 3.41 (3H, s), 2.37 (2H, q), 0.96 (3H, t).

[1826] Present compound 105: 1H-NMR (DMSO-D6) δ: 8.56 (1H, s), 7.73 (1H, t), 7.56-7.52 (3H, m), 7.43-7.42 (2H, m), 3.41 (3H, s), 2.37 (2H, q), 0.96 (3H, t).

[1827] Present compound 106: 1H-NMR (CDCl3) δ: 8.31-8.27 (1H, m), 7.57-7.31 (6H, m), 4.06 (2H, q), 2.33 (2H, q), 1.32 (3H, t), 1.10 (3H, t).

[1828] Present compound 107: 1H-NMR (CDCl3) δ: 8.31-8.28 (1H, m), 7.59-7.38 (6H, m), 3.92 (2H, d), 2.33 (2H, q), 1.26-1.17 (1H, m), 1.10 (3H, t), 0.45-0.43 (2H, m), 0.24-0.23 (2H, m).

[1829] Present compound 108: 1H-NMR (CDCl3) δ: 8.33-8.32 (1H, m), 7.60-7.44 (6H, m), 4.93 (2H, s), 2.52 (2H, q), 1.16 (3H, t).

[1830] Present compound 113: 1H-NMR (CDCl3) δ: 8.40-8.39 (1H, m), 7.80-7.78 (1H, m), 7.62-7.59 (1H, m), 7.54-7.51 (2H, m), 7.40-7.38 (1H, m), 7.25 (1H, t), 3.54 (3H, s), 2.45 (2H, q), 1.12 (3H, t).

[1831] Present compound 114: 1H-NMR (CDCl3) δ: 8.52-8.51 (1H, m), 7.90-7.88 (2H, m), 7.73-7.70 (2H, m), 7.51-7.49 (1H, m), 3.59 (3H, s), 2.50 (2H, q), 1.13 (3H, t).

[1832] Present compound 115: 1H-NMR (CDCl3) δ: 7.90 (2H, s), 7.70 (1H, s), 7.66 (1H, d), 7.49 (1H, d), 7.13 (1H, dd), 3.83 (3H, s), 3.57 (3H, s), 2.45 (2H, q), 1.11 (3H, t).

[1833] Present compound 116: 1H-NMR (DMSO-D6) δ: 8.59-8.58 (1H, m), 7.68-7.57 (2H, m), 7.32-7.26 (4H, m), 3.39 (3H, s), 2.48-2.43 (2H, q), 0.97 (3H, t).

[1834] Present compound 117: 1H-NMR (DMSO-D6) δ: 8.60-8.60 (1H, m), 7.69-7.58 (2H, m), 7.37-7.35 (2H, m), 7.22-7.14 (2H, m), 3.39 (3H, s), 2.49-2.43 (2H, q), 0.96 (3H, t).

[1835] Present compound 118: 1H-NMR (CDCl3) δ: 8.45-8.44 (1H, m), 7.55-7.52 (1H, m), 7.41-7.38 (1H, m), 7.12-7.08 (2H, m), 3.51 (3H, s), 2.49 (2H, q), 1.13 (3H, t).

[1836] Present compound 119: 1H-NMR (CDCl3) δ: 8.18-8.16 (1H, m), 7.58-7.20 (11H, m), 5.27 (2H, s), 1.68-1.66 (2H, m), 0.81 (3H, t).

[1837] Present compound 120: 1H-NMR (CDCl3) δ: 8.52-8.51 (1H, m), 8.49-8.47 (1H, m), 8.17-8.16 (1H, m), 7.97-7.95 (1H, m), 7.59-7.51 (3H, m), 7.42-7.40 (3H, m), 7.26-7.24 (1H, m), 5.27 (2H, s), 1.76 (2H, q), 0.84 (3H, t).

[1838] Present compound 121: 1H-NMR (CDCl3) δ: 8.42-8.41 (1H, m), 7.53-7.37 (2H, m), 7.08-7.07 (2H, m), 6.78-6.76 (1H, m), 6.53-6.17 (2H, m), 3.53 (3H, s), 2.42 (2H, q), 1.11 (3H, t).

[1839] Present compound 122: 1H-NMR (CDCl3) δ: 8.43-8.42 (1H, m), 7.66-7.65 (1H, m), 7.54-7.51 (2H, m), 6.95-6.93 (1H, m), 6.64-6.28 (2H, m), 3.52 (3H, s), 2.41 (2H, q), 1.11 (3H, t).

[1840] Present compound 123: 1H-NMR (CDCl3) δ: 8.42-8.42 (1H, m), 7.55-7.51 (5H, m), 7.40-7.38 (1H, m), 3.54 (3H, s), 2.40 (2H, q), 1.10 (3H, t).

[1841] Present compound 124: LCMS: 618 [M+H]+, RT=2.40 minPreparation Example 1-2

[1842] The compounds prepared according to the Reference Preparation Example 3 and physical properties thereof are shown below.A Compound Represented by Formula (B-2)

[1843]

[1844] wherein the combination of A2, A3, A4, A5, G4, R1, R3b and n represents any one combination indicated in Table B-2 and Table B-3.

[1845] TABLE B-2PresentcompoundA2A3A4A5G4R1R3bn29C-BrCHC-CF3CHCHMeI130C-ClCHC-ClCHCHMeI131CHC-CF3CHCHCHMeBr235C-SCF3CHCHCHCHMeCF3236C-SCF3CHCHCHCHMeCl239CHC-SCF3CHCHCHMeI240CHC-SCF3CHCHNMeH245C-ICHCHCHCHMeBr247CHC-OCF3CHCHCHMeCl248CHC-OCH2CF3CHCHCHMeCl249CHC-CNCHCHCHMeBr250C-CF3CHC-CF3CHCHMeI253BrCHBrCHCHMeI254BrCHNCHCHMeI255C-ClCHC-ClCHCHMeI266C-OCF3CHCHCHCHMeBr269C-CF3CHCHNCHMeBr270C-CF3CHC-CF3CHCHMeI171C-CF3CHNCHCHMeI172C-CF3CHNCHCHMeI274C-CF3CHCHNCHMeI279C -CNCHCHCHCHMeI280C-CF3CHC-CF3CHCHCH2CNI281CHC-SCF3CHCHCHMeBr182CHC-CF3CHCHCHMeBr188C-C2F5CHCHCHCHMeI294CHC-OCF3CHCHCHMeBr195C-OCF3CHCHCHCHMeBr197C-ICHC-ICHCHMeI198CHC-OCF2HCHCHCHMeBr199C-OCF2HCHCHCHCHMeBr1100CHC-OCF2HCHCHCHMeBr2101C-OCF2HCHCHCHCHMeBr2109CHC-CF3CHCHCHEtBr2110CHC-CF3CHCHCHCH2CPrBr2111CHC-CF3CHCHCHCH2CNBr2112CHCHC-CF3NCHMeBr2125C-CF3CHC-CF3CHCHMeCF32126C-CF3CHC-CF3CHCHEtI2127C-CF3CHC-CF3CHCHCH2CPrI2128C-CF3CHC-CF3CHCHCH2OEtI2129CHC-CF3CHCHCHMeCF32130CHC-CF3CHCHCHMeCl2131CHC-ClCHCHCHMeBr1132CHC-ICHCHCHMeBr1133C-ICHCHCHCHMeBr1134CHC-SCF3CHCHCHMeCF31135CHC-CF3CHCHCHBnBr2136CHC-CF3CHCHCHCH2Py3Br2(N-oxide)137C-OCF2HCHC-OCF2HCHCHMeI2138C-FC-OCF2HCHCHCHMeI2139CHC-SF5CHCHCHMeI2140CHC-ClCHCHCHMeBr2141CHC-ICHCHCHMeBr2142C-ClCHCHCHCHMeBr1143C-ClCHCHCHCHMeBr2

[1846] Present compound 29: 1H-NMR (CDCl3) δ: 8.99 (1H, s), 7.84 (1H, s), 7.77 (1H, s), 7.67-7.60 (2H, m), 7.47 (1H, d), 3.53 (3H, s), 3.48-3.33 (1H, m), 2.90-2.40 (1H, m), 1.41-1.30 (3H, m).

[1847] Present compound 30: 1H-NMR (CDCl3) δ: 9.00 (1H, s), 7.62 (1H, dq), 7.46 (1H, dd), 7.40-7.30 (3H, m), 3.59-3.33 (4H, m), 2.95-2.43 (1H, m), 1.43-1.32 (3H, m).

[1848] Present compound 31: 1H-NMR (CDCl3) δ: 8.90 (1H, s), 7.84-7.51 (6H, m), 3.71-3.22 (5H, m), 1.42-1.29 (3H, m).

[1849] Present compound 35: 1H-NMR (CDCl3) δ: 9.10 (1H, s), 7.98 (1H, d), 7.90-7.67 (5H, m), 3.56-3.34 (5H, m), 1.40-1.36 (3H, m).

[1850] Present compound 36: 1H-NMR (CDCl3) δ: 8.77 (1H, s), 7.82 (1H, d), 7.73-7.42 (5H, m), 3.60-3.19 (5H, m), 1.30-1.26 (3H, m).

[1851] Present compound 39: 1H-NMR (CDCl3) δ: 8.95 (1H, s), 7.71-7.65 (5H, m), 7.50 (1H, d), 3.61-3.27 (5H, m), 1.43-1.17 (3H, m).

[1852] Present compound 45: 1H-NMR (CDCl3) δ: 8.89 (1H, s), 7.99-7.50 (6H, m), 3.58-3.26 (5H, m), 1.44-1.30 (3H, m).

[1853] Present compound 47: 1H-NMR (CDCl3) δ: 8.81 (1H, s), 7.69-7.68 (4H, m), 7.51 (1H, d), 7.26-7.25 (1H, m), 3.57-3.34 (5H, m), 1.38-1.33 (3H, m).

[1854] Present compound 48: 1H-NMR (CDCl3) δ: 8.81 (1H, s), 7.64-7.53 (5H, m), 6.98-6.93 (1H, m), 4.39-4.37 (2H, m), 3.47-3.40 (5H, m), 1.31-1.30 (3H, m).

[1855] Present compound 49: 1H-NMR (CDCl3) δ: 8.89 (1H, s), 7.78-7.67 (6H, m), 3.46-3.31 (5H, m), 1.38-1.35 (3H, m).

[1856] Present compound 50: 1H-NMR (CDCl3) δ: 8.92 (1H, s), 8.13-7.76 (3H, m), 7.71 (1H, d), 7.50 (1H, d), 3.58-2.91 (5H, m), 1.46-1.28 (3H, m).

[1857] Present compound 53: 1H-NMR (CDCl3) δ: 9.04-8.92 (1H, m), 7.80-7.59 (4H, m), 7.51 (1H, dd), 3.59-3.16 (5H, m), 1.29-1.23 (3H, m).

[1858] Present compound 54: 1H-NMR (CDCl3) δ: 9.07-8.43 (3H, m), 8.14-8.11 (1H, m), 7.72 (1H, dd), 7.51 (1H, dd), 3.79-2.63 (5H, m), 1.45-1.24 (3H, m).

[1859] Present compound 55: 1H-NMR (CDCl3) δ: 9.05-8.87 (1H, m), 7.70 (1H, dd), 7.55-7.36 (4H, m), 3.66-2.79 (5H, m), 1.45-1.32 (3H, m).

[1860] Present compound 66: 1H-NMR (CDCl3) δ: 8.87 (1H, s), 8.05-7.37 (6H, m), 3.51-3.43 (5H, m), 1.29 (3H, t).

[1861] Present compound 69: 1H-NMR (CDCl3) δ: 9.17 (1H, s), 8.45-8.21 (2H, m), 7.72-7.43 (3H, m), 3.69 (3H, s), 3.58-3.39 (2H, m), 1.52-1.40 (3H, m).

[1862] Present compound 70: 1H-NMR (CDCl3) δ: 8.96 (1H, s), 7.97-7.92 (2H, m), 7.87 (1H, s), 7.63 (1H, d), 7.46 (1H, d), 3.60-3.29 (5H, m), 1.30 (3H, t).

[1863] Present compound 71: 1H-NMR (CDCl3) δ: 8.72 (1H, s), 8.63 (1H, s), 8.53 (1H, s), 7.92 (1H, s), 7.41 (1H, dd), 7.23 (1H, dd), 3.15 (2H, br s), 2.47 (3H, br s), 1.05 (3H, d).

[1864] Present compound 72: 1H-NMR (CDCl3) δ: 9.10-8.63 (3H, br m), 8.21 (1H, s), 7.72 (1H, dd), 7.51 (1H, dd), 3.58-2.76 (5H, br m), 1.57-1.54 (3H, br m).

[1865] Present compound 74: 1H-NMR (CDCl3) δ: 9.17 (1H, s), 8.40-7.92 (2H, m), 7.64-7.31 (3H, m), 3.64-3.28 (5H, m), 1.42-1.30 (3H, m).

[1866] Present compound 79: LCMS: 495 [M+H]+, RT=1.68 min

[1867] Present compound 80: LCMS: 631 [M+H]+, RT=2.07 min

[1868] Present compound 81: 1H-NMR (DMSO-D6) δ: 8.85 (1H, s), 7.80 (1H, d), 7.73 (1H, dd), 7.68 (2H, d), 7.50 (2H, d), 3.52-3.41 (5H, m), 1.10 (3H, t).

[1869] Present compound 82: 1H-NMR (DMSO-D6) δ: 8.84 (1H, s), 7.80 (1H, dd), 7.74-7.71 (3H, m), 7.58 (2H, d), 3.52-3.40 (5H, m), 1.10 (3H, t).

[1870] Present compound 88: LCMS: 588 [M+H]+, RT=2.03 min

[1871] Present compound 94: LCMS: 490 [M+H]+, RT=1.78 min

[1872] Present compound 95: LCMS: 490 [M+H]+, RT=1.79 min

[1873] Present compound 97: 1H-NMR (CDCl3) δ: 9.02-9.00 (1H, m), 8.08-8.06 (1H, m), 7.82-7.77 (2H, m), 7.64-7.61 (1H, m), 7.48-7.45 (1H, m), 3.51 (3H, s), 3.49-3.37 (2H, br m), 1.41 (3H, t).

[1874] Present compound 98: LCMS: 472 [M+H]+, RT=1.62 min

[1875] Present compound 99: LCMS: 472 [M+H]+, RT=1.62 min

[1876] Present compound 100: LCMS: 488 [M+H]+, RT=1.78 min

[1877] Present compound 101: LCMS: 488 [M+H]+, RT=1.78 min

[1878] Present compound 109: LCMS: 504 [M+H]+, RT=1.98 m...

Claims

1. A compound represented by formula (I)wherein:Z represents an oxygen atom or a sulfur atom;R1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group U, a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, C(O)R51C(O)OR51, or C(O)NR51R52,R51 and R52 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, or a hydrogen atom;R2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;n represents 0, 1, or 2;G1 represents a nitrogen atom or CR3a:G2 represents a nitrogen atom or CR3b;G3 represents a nitrogen atom or CR3e;G4 represents a nitrogen atom or CR3d;R3a, R3b, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group E, a phenyl group optionally substituted with one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group H, OR12, NR11R12, NR11aR12a NR24NR11R12, NR24OR11, NR11C(O)R13, NR24NR11C(O)R13, NR11C(O)OR14, NR24NR11C(O)OR14, NR11C(O)NR31R32, NR24NR11C(O)NR31R32, N═CHNR31R32, N═S(O)pR15R16, C(O)R13, C(O)OR17, C(O)NR31R32, C(O)NR11S(O)2R23, CR30═NOR17 NR11CR24═NOR17, S(O)mR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom;p represents 0 or 1;m represents 0, 1, or 2;R30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a halogen atom, OR35, NR36R37, or a hydrogen atom;R35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);R17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;R11, R24, R36, and R37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom;R12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group J, a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a hydrogen atom, or S(O)2R23;R23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s) or a phenyl group optionally substituted with one or more substituent(s) selected from Group D;RH11a and R12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E;R13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;R14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), or a phenyl C1-C3 alkyl wherein, the phenyl moiety in said phenyl C1-C3 alkyl group optionally being substituted with one or more substituent(s) selected from Group D;R15 and R16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);R31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;R32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, S(O)2R23, or a hydrogen atom;A1 represents a nitrogen atom or CR4a;A2 represents a nitrogen atom or CR4b;A3 represents a nitrogen atom or CR4c;A4 represents a nitrogen atom or CR4d;A5 represents a nitrogen atom or CR4e:provided that not all of A2, A3, and A4 represent nitrogen atoms;R4a and R4e are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O), R41, S(O)2NR41R42, NR41R43 NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;when A5 represents CR4c, R4e and R1 are optionally combined with each other to form-NR45—CR41R42 representing the binding position to the nitrogen atom to which R1 is bound;R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O), R41, S(O)2NR41R42, NR41R42 NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;provided that not all of present R4a, R4b, R4c, R4d, and R4e represent hydrogen atoms;k represents 0, 1, or 2;q represents 0, 1, or 2;R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;R43 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, or a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z;R44 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W2, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, C(O)R46, C(O)OR46, C(O)NR46R47, or a hydrogen atom; andR46 and R47 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;Group B: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a cyano group, a hydroxy group, and a halogen atom;Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), and a halogen atom;Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom;R21 and R22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;Group F: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group C, an amino group, NHR21, NR21R22, a halogen atom, and a cyano group;Group H: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, OR10, NR9R10, C(O)R10, C(O)NR10R10 OC(O)R9, OC(O)OR9, NR10C(O)R9, NR10C(O)OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, and an amino group;R9 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s) or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s);R10 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;Group J: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, and a cyano group;Group U: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;Group V: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;Group W: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a cyano group, and a halogen atom;Group X: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom;Group Y: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;Group Z: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;Group W2: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom,or an N-oxide thereof.

2. The compound or an N-oxide thereof according to claim 1, whereinR45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, C(O)R46, C(O)OR46, C(O)NR46R47, or a hydrogen atom.

3. The compound or an N-oxide thereof according to claim 1, whereinG1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents a nitrogen atom or CR34.

4. The compound or an N-oxide thereof according to claim 1, whereinA1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom or CR4c, A4 represents a nitrogen atom or CR4d, and A5 represents a nitrogen atom or CR4e.

5. The compound or an N-oxide thereof according to claim 1, whereinthe combination of A1, A2, A3, A4, and A5 represents:a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR44, and A5 represents CR4e;a combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents a nitrogen atom, A4 represents CR44, and A5 represents CR4e;a combination wherein A1 represents CR42, A2 represents CR4b, A3 represents CR4c, A4 represents a nitrogen atom, and A5 represents CR4e; ora combination wherein A1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR44, and A5 represents a nitrogen atom.

6. The compound or an N-oxide thereof according to claim 1, whereinA1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR44, and A5 represents CR4e.

7. The compound or an N-oxide thereof according to claim 1, whereinG1 represents CR3a, G2 represents CR3b, G3 represents CR3c, and G4 represents CR3d; andA1 represents CR4a, A2 represents CR4b, A3 represents CR4c, A4 represents CR44, and A5 represents CR4c.

8. The compound or an N-oxide thereof according to claim 1, wherein R2 represents an ethyl group.

9. The compound or an N-oxide thereof according to claim 1, wherein Z represents an oxygen atom.

10. A composition for controlling a harmful arthropod comprising the compound or an N-oxide thereof according to claim 1.

11. A composition comprising one or more ingredient(s) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the compound or an N-oxide thereof according to claim 1:Group (a): a group consisting of insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients;Group (b): fungicidal active ingredients;Group (c): plant growth regulatory ingredients;Group (d): repellent ingredients.

12. A seed or a vegetative reproductive organ holding an effective amount of the composition according to claim 11.

13. A method for controlling a harmful arthropod which comprises applying an effective amount of the composition according to claim 11 to a harmful arthropod or a habitat where a harmful arthropod lives.

14. A seed or a vegetative reproductive organ, comprising:an effective amount of the compound or an N-oxide thereof according to claim 1.

15. A method for controlling a harmful arthropod which comprises applying an effective amount of the compound or an N-oxide thereof according to claim 1 to a harmful arthropod or a habitat where a harmful arthropod lives.

16. A compound represented by formula (II)wherein:Z represents an oxygen atom or a sulfur atom;R2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;n represents 0, 1, or 2;G1 represents a nitrogen atom or CR3a;G2 represents a nitrogen atom or CR3b;G3 represents a nitrogen atom or CR3c;G4 represents a nitrogen atom or CR3d;R3a, R35, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group E, a phenyl group optionally substituted with one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group H, OR12, NR11R12, NR11aR12a NR24NR11R12, NR24OR11, NR11C(O)R13, NR24NR11C(O)R13, NR11C(O)OR14, NR24NR11C(O)OR14, NR11C(O)NR31R32, NR24NR11C(O)NR31R32, N═CHNR31R32, N═S(O)pR15R16, C(O)R13, C(O)OR17, C(O)NR31R32, C(O)NR11S(O)2R23, CR30═NOR17, NR11CR24═NOR17, S(O)mR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom;p represents 0 or 1;m represents 0, 1, or 2;R30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a halogen atom, OR35, NR36R37, or a hydrogen atom;R35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);R17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;R11, R24, R36, and R37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom,R12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group J, a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a hydrogen atom, or S(O)2R23,R23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s) or a phenyl group optionally substituted with one or more substituent(s) selected from Group D;R11a and R12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E;R13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;R14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), or a phenyl C1-C3 alkyl group, the phenyl moiety in said phenyl C1-C3 alkyl group optionally being substituted with one or more substituent(s) selected from Group D;R15 and R16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);R31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;R32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, S(O)2R23, or a hydrogen atom;A1 represents a nitrogen atom or CR4a;A2 represents a nitrogen atom or CR4b;A3 represents a nitrogen atom or CR4c;A4 represents a nitrogen atom or CR4d;A5 represents a nitrogen atom or CR4e:provided that not all of A2, A3, and A4 represent nitrogen atoms;R4a and R4e are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O); R41, S(O)2NR41R42, NR41R43 NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42 CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O), R41, S(O)2NR41R42, NR41R42 NR41C(O)R42, NR41C(O)OR42, NR41S(O)R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;provided that not all of present R4a, R4b, R4c, R4d, and R4e represent hydrogen atoms;k represents 0, 1, or 2;q represents 0, 1, or 2;R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;R43 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, or a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z; andR44 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);Group B: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a cyano group, a hydroxy group, and a halogen atom;Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), and a halogen atom;Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom;R21 and R22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;Group F: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group C, an amino group, NHR21, NR21R22, a halogen atom, and a cyano group;Group H: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, OR10, NR9R10C, C(O)R10, C(O)NR9R10, OC(O)R9, OC(O)OR9, NR10C(O) R10, NR10C(O) OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, and an amino group;R9 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s) or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s);R10 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;Group J: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, and a cyano group;Group X: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom;Group Y: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;Group Z: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom,or a salt thereof.

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